Research on new synthetic routes about 658-89-9

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethoxy)benzene-1,2-diamine, and friends who are interested can also refer to it.

Application of 658-89-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 658-89-9 name is 4-(Trifluoromethoxy)benzene-1,2-diamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 41 : Mixture of (trans) N-{2-amino-4-[(trifluoromethyl)oxy1phenyl)-3-(4- fluorophenyl)-2-oxo-1-oxa-3-azaspiro[4.51decane-8-carboxamide and (trans) N-{2-amino- 5-[(trifluoromethyl)oxy1phenyl)-3-(4-fluorophenyl)-2-oxo-1-oxa-3-azaspiro[4.51decane-8- carboxamide; 4-[(Trifluoromethyl)oxy]-1 ,2-benzenediamine (Intermediate 32, 177 mg, 0.921 mmol) and (trans) 3-(4-fluorophenyl)-2-oxo-1-oxa-3-azaspiro[4.5]decane-8-carboxylic acid (Intermediate 42, 180 mg, 0.614 mmol) were dissolved in pyridine (2.5 ml) and EDC (188 mg, 0.982 mmol) was added. The mixture was stirred at r.t. for 2 hours. The pyridine was removed under vacuum and the residue partioned between aq. sat. NaHCO3 (20 ml) and EtOAc (50 ml). The aqueous layer was extracted once again with EtOAc (30 ml). The combined EtOAc extracts were washed with brine (20 ml), dried (Na2SO4), filtered and evaporated. The residue was purified by silica gel chromatography eluting with cyclohexaneEtOAc 64 to 46. The title compounds were obtained as a mixture of both possible regioisomers and were collected together to give 274.5 mg (0.529 mmol, 86%). 1 H-NMR (400 MHz, CDCI3): (data given for major isomer) delta 7.54 (2H, dd), 7.18-7.25 (1 H, m), 7.19 (2H, t), 6.64-6.73 (1 H, m), 3.77 (2H, s), 2.48-2.58 (1 H, m), 2.10-2.23 (4H, m), 1.80-2.00 (4H, m), one aromatic proton not detected, might fall underneath CHCI3 signal; UPLC-MS: 0.75 min, 468 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethoxy)benzene-1,2-diamine, and friends who are interested can also refer to it.

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