Category: 658-89-9

Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 4-(Trifluoromethoxy)benzene-1,2-diamine

Intermediate 67: Mixture of (trans)-N-{2-amino-4-r(trifluoromethyl)oxylphenyl)-2-oxo-3-(3- pyridinyl)-1-oxa-3-azaspiror4.5ldecane-8-carboxamide and (trans)-N-{2-amino-5- [(trifluoromethvDoxyiphenvD^-oxo-S-O-pyridinvD-i-oxa-S-azaspiroK.deltaidecane-delta- carboxamide; Lithium (trans)-2-oxo-3-(3-pyridinyl)-1-oxa-3-azaspiro[4.5]decane-8-carboxylate (Intermediate 66, 75 mg, 0.251 mmol) and EDC (77 mg, 0.401 mmol) were suspended in pyridine (2 ml) and stirred for 30 min. 4-[(trifluoromethyl)oxy]-1 ,2-benzenediamine (Intermediate 32, 72.2 mg, 0.376 mmol) was then added and the resulting dark solution was stirred overnight at r.t. Solvent was removed under vacuum, taken up with DCM (20 ml) and washed with saturated NaHCO3 solution (2X5 ml). The organic phase was concentrated under vacuum to afford a crude oil. The crude was purified by flash chromatography on Biotage SP1 (25+M column, NH cartridge) eluting in gradient with CyclohexaneEtOAc. The title compound was eluted with 100% EtOAc and recovered as colourless solid (60 mg) as mixture of regioisomers with unknown ratio. 1 H-NMR (400 MHz, CD3OD): delta 8.88 (br s, 2H), 8.34-8.32 (m, 2H), 8.13 (dq, 2H), 7.50-7.45 (m, 2H), 7.18-7.14 (m, 2H), 6.97-6.95 (m, 1 H), 6.75-6.73 (m, 1 H), 6.58-6.53 (m, 2H), 3.74 (s, 4H), 2.68-1.68 (m, 18 H); UPLC-MS: 0.60 min, mz 226 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 658-89-9, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, A new synthetic method of this compound is introduced below., Formula: C7H7F3N2O

[0373] Compounds 41 and 100: To a mixture of Comp-41a and Comp-lOOa mixture (0.3 g, 1.31 mmol) and Comp-3b (0.29 g, 1.31 mmol) was added i-BuOk (1 mL, 1M in THF) and the reaction mixture was heated at 50 C for 16 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with w?ater and extracted with EtOAc (50 mL X 2). The organic layer was washed with water, brine, separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude obtained was purified by prep HPLC purification to afford a mixture of regioisomers (E)-2-(2-(2,5- dimethyl-l-(l-methylpiperidin-4-yl)-lH-pyrrol-3-yl)vinyl)-7-(trifluoromethoxy)quinoxaline and (E)-2-(2-(2,5-dimethyl-l-(l-methylpiperidin-4-yl)-1H-pyrrol-3-yl)vinyl)-6- (0655) (trifluoromethoxy)quinoxaline (41 and 100, respectively; 0.09 g, 17%) as a yellow solid. (0656) [0374] HPLC purity : 98.19% (0657) [0375] MS (ESI) m/e [M+H]+/Rt/%: 431.20/1.69/97.8% (0658) [0376] 1H NMR (400 MHz, DMSO-d6, 2: l mixture of isomers) delta 1.73 (d, J=l 1.25 Hz, 2H), 2.01 – 2.11 (m, 2H), 2.14-2.17 (m, 2H), 2.23 (s, 3H), 2.29 (s, 3H), 2.44 (s, 3H), 2.91 (d, J=10.27 Hz, 2H), 3.92 – 4.02 (m, 1H), 6.24 (s, 1H), 6.85 (d, J=15.65 Hz, 1H), 7.62 – 7.78 (m, 1H), 7.85 (s, 1H), 7.91 – 7.98 (m, 1H), 8.04 – 8.13 (m, 1H), 9.24 & 9.28 (s, 0.56H & 0.34H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. COA of Formula: C7H7F3N2O

A mixture of S-bromo-lH-pyrazoloP^-bjpyridine-S-carboxyric acid Compound Ic (0.68 g, 1.93 mmol), Compound 16b (0.373 g, 1.93 mmol), HATU (0.73 g, 1.9 mmol) and DIPEA (1 mL, 5.8 mmol) in DMF (30 mL) was stirred at room temperature overnight. The solvent was removed under vacuum and the resulting yellow residue was mixed with AcOEt, sequentially washed with saturated aqueous NH4Cl, IM HCl, water and saturated aqueous NaHCO3, then dried over Na2SO4. The solvent was evaporated to dryness to provide 5-bromo-lH-pyrazolo[3,4-b]pyridine-3- carboxylic acid (2-amino-4-trifluoromethoxy-phenyl)-amide Compound 16c (0.67 g, 83% yield) as a yellow solid. LC-MS major peak 3.03 min, MS (ESI) m/z 416.0 (M+)/417.0 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 658-89-9, its application will become more common.

Reference of 658-89-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Aryl-5-trifluoromethoxybenzimidazole. The modified procedure of Bahrami, K. et. al. (Bahrami K., Khodaei M. M., Kavianinia I. Synthesis 2007, p. 547-550) was used. A solution of 2-amino-4-trifluoromethoxyaniline (0.7 g, 0.0036 Mol) in acetonitrile -CH3CN (5 mL) was mixed with aldehyde (0.0037 Mol) in CH3CN (5 mL) at 20 C. and stirred for 5-10 min. Aqueous 30% H2O2 (0.025 Mol) and concentrated 35% aqueous HCl (0.0126 Mol) were added at 20 C. and the mixture was stirred at this temperature for the 2-5 h (the progress of the reaction was monitored by TLC). Precipitate formed was filtered, washed with CH3CN (2×10 mL) and dried.2-Phenyl-5-trifluoromethoxybenzimidazole. Benzaldehyde was used, Ar=C6H5. Yield 0.76 g (71 wt. %). M.p. 208-210 C. 1H NMR (DMSO-d6): 7.31 (d, J=8.5 Hz, 1H), 7.38 (m, 2H), 7.49 (t, J=8.5 Hz, 1H), 7.83 (s, 1H), 7.95 (d, J=8.5 Hz, 1H), 8.57 (d, J=7.0 Hz, 2H). 13C NMR (DMSO-d6): 107.87, 115.26, 116.42, 120.21 (q, J=255.1 Hz), 126.90, 127.98, 128.84, 130.73, 135.91, 138.10, 144.17, 152.51. 19F NMR (DMSO-d6): -57.60. [M+1]+ 279.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(Trifluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference of 658-89-9, The chemical industry reduces the impact on the environment during synthesis 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

Intermediate 51 : Mixture of (trans)-N-{2-amino-4-[(trifluoromethyl)oxy1phenyl)-3-(6-methyl- 2-pyridinyl)-2-oxo-1-oxa-3-azaspiro[4.51decane-8-carboxamide and (trans)-N-{2-amino-5- [(trifluoromethyl)oxy1phenyl)-3-(6-methyl-2-pyridinyl)-2-oxo-1-oxa-3-azaspiro[4.51decane- 8-carboxamide; To a shaken mixture of (trans)-3-(6-methyl-2-pyridinyl)-2-oxo-1-oxa-3- azaspiro[4.5]decane-8-carboxylic acid (Intermediate 52, 65.4 mg, 0.225 mmol) and 4- [(trifluoromethyl)oxy]-1 ,2-benzenediamine (Intermediate 32, 64.9 mg, 0.338 mmol) in pyridine (1.5 ml) was added EDCHCI (86 mg, 0.451 mmol) and the mixture was shaken for 2 hours. The mixture was concentrated under vacuum; the residue was partitioned between saturated sodium bicarbonate solution and EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under vacuum to give a residue. The residue was purified twice by silica gel chromatography (elution in gradient with 0-100% Et2ODCM) to afford the title compound as brown residue (98 mg, 80%). No further purification followed. UPLC-MS: 0.76 min, m/z 465 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(Trifluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-(Trifluoromethoxy)benzene-1,2-diamine

To a mixture of 4-(trifluoromethoxy)benzene-1,2-diamine (0.1 g, 521 imol, 1 eq) in 2 mL of dichloromethanecooled to 0C was added methyl 2,2,2-trichloroethanimidate (119 mg, 676 imol, 1.3 eq), TFA(148 mg, 1.3 mmol, 2.5 eq) successively. The mixture was stirred at 25C for 12 hours underN2 atmosphere. The mixture was filtered and the filtrate was purified by prep-TLC (Si02,eluting with petroleum ether: ethyl acetate = 2:1) to give a 0.1 g of compound J-3 (44% yield,TFA salt) as a yellow solid.

According to the analysis of related databases, 658-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 658-89-9,Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: The mixture of o-phenylenediamine (1) and cyanoacetamide (2) were stirred in 200 C for 30 min without any solvent. After cooling, the mixture was dissolved in ethanol. The crude product was purified by silica gel column chromatography using dichloromethane-methanol (60:1) as eluant to give the pure compound 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethoxy)benzene-1,2-diamine, its application will become more common.

Reference:
Article; Pan, Ting; He, Xin; Chen, Bing; Chen, Hui; Geng, Guannan; Luo, Haihua; Zhang, Hui; Bai, Chuan; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 500 – 513;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 658-89-9,Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred solution of N-boc-O-methyl-L-threonine (1.99 g, 8.53 mmol) in acetonitrile (27 ml) at 0C was added N-methylmorpholine (1.3 ml, 12.0 mmol) followed by the dropwise addition of isobutyl chloroformate (1.3 ml, 10 mmol). The reaction mixture was stirred at 0C for 45 minutes. 4-(Trifluoromethoxy)benzene-1,2-diamine (1.64 g, 8.53 mmol) was dissolved in acetonitrile (14 mL) and cooled to 0C. To this was added the solution of the activated N-Boc-O-methyl-L-threonine via a dropping funnel fitted with a cotton wool plug. After the addition was complete the dropping funnel and cotton wool plug was rinsed with acetonitrile (10 mL) and was stirred at room temperature overnight. The reaction concentrated in vacuo, then diluted with EtOAc (80 mL) and citric acid (40 mL, 5% aqueous solution) was added. The organics were separated, washed with citric acid (40 mL, 5% aqueous solution), followed by brine (20 mL), dried over sodium sulphate and reduced in volume to afford an orange solid (3.69 g) which was used without further purification (mix of regioisomers). tert-Butyl ((1R,2R)-2-methoxy-1-(6-(trifluoromethoxy)-1H-benzo[d]imidazol-2-yl)propyl)carbamate. A mixture of tert-butyl ((2S,3R)-1-((2-amino-4-(trifluoromethoxy)phenyl)amino)-3-methoxy-1-oxobutan-2-yl)carbamate and tert-butyl ((2S,3R)-1-((2-amino-5-(trifluoromethoxy)phenyl)amino)-3-methoxy-1-oxobutan-2-yl)carbamate (3.48 g, 8.54 mmol) was diluted with acetic acid (33 ml) and stirred at room temperature for 4.5 days. The reaction was quenched by slow addition of a K2CO3 solution (10% aqueous solution, 50 ml) and EtOAc (50 ml) was added. The organics were separated, combined and washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo to afford a dark brown gum which was purified by column chromatography (120g ISCO column, 0-30% EtOAc/heptane) to obtain 1.64 g (49%) of the title compound as a solid. This was taken on to next step without further purification. 1H NMR (400 MHz, DMSO-d6) delta 12.43 (br. s., 1H), 7.54 (br. s., 2H), 7.13 (br. s., 1H), 7.02 (d, J=7.81 Hz, 1H), 4.83 (dd, J=4.98, 8.10 Hz, 1H), 3.72-3.85 (m, 1H), 3.21 (s, 3H), 1.38 (s, 9H), 1.02 (d, J=6.25 Hz, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethoxy)benzene-1,2-diamine, its application will become more common.

Reference:
Article; Brown, Alan D.; Bagal, Sharan K.; Blackwell, Paul; Blakemore, David C.; Brown, Bruce; Bungay, Peter J.; Corless, Martin; Crawforth, James; Fengas, David; Fenwick, David R.; Gray, Victoria; Kemp, Mark; Klute, Wolfgang; Malet Sanz, Laia; Miller, Duncan; Murata, Yoshihisa; Payne, C. Elizabeth; Skerratt, Sarah; Stevens, Edward B.; Warmus, Joseph S.; Bioorganic and Medicinal Chemistry; vol. 27; 1; (2019); p. 230 – 239;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 658-89-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 18 (SV2-Nitro-6-f4-(5-trifluoromethoxy-1H-benzoimida2ol-2-yl)-benzyloxy1 -6.7-dihvdro-5H-imidazor2.1-bin .3l oxazine (23)23In an inert atmosphere, 4-((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b)[1 ,3]oxazin-6- yloxymethyl)-benzoic acid (100 mol%) is dissolved in anhydrous CH2CI2 (0.20 M) and added HATU (120 mol%) and DIEA (120 mol%). Reaction is stirred at room temperature for 5 min followed by addition of 1,2-diamino-substituted benzene (120 mol%). Resulting reaction mixture is stirred at room temperature overnight. Reaction is concentrated and dissolved in EtOAc and washed with water three times. Organic layer is dried under anhydrous Na2SO4 and concentrated to yield pale brown solid, which is dissolved in glacial acetic acid (0.36 M). Reaction mixture is heated to 95 ‘C for 30 min. Crude reaction mixture is concentrated and residue obtained is purified by preparative reverse-phase LC to give final compound as fluffy solid. MS: M+ 476.4.1H NMR (CD3OH1 400 MHz): delta 8.05 (d. J = 8.18 Hz, 2H), 7.74 (s, 1 H), 7.62 (d, J = 8.76 Hz, 1H), 7.50 (m, 3H)1 7.18 (dd, J = 8.73, 1.24 Hz, 1H), 4.87 (s, 2H)1 4.73 (m, 2H)1 4.48 (d, J = 12.05 Hz, 1H), 4.30 (m, 2H). Melting Point: 98-99 ‘C. [Q]21D = -37.81 (C= 0.003, MeOH).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(Trifluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; US DEPARTMENT OF HEALTH & HUMAN SERVICES; WO2007/75872; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H7F3N2O

Step a. To a solution of 4-(trifluoromethoxy)benzene-l,2-diamine (CAS Number 658-89-9; 0.45 g, 2.34 mmol) in DMF (5 ml) was added urea (0.28 g, 4.66 mmol) at rt. The resulting reaction mixture was heated at 150C for 20 h. The reaction mixture was diluted with water (5 ml) and the brown precipitate was collected by vacuum filtration and dried under reduced pressure to yield 5- (trifluoromethoxy)-l,3-dihydro-2H-benzo[d]imidazol-2-one (0.28 g, 1.28 mmol). LCMS: Method C, 2.118 min, MS: ES+ 219.

The synthetic route of 658-89-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; STOCKLEY, Martin Lee; KEMP, Mark Ian; MADIN, Andrew; (88 pag.)WO2018/60742; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem