These common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, its 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. name: 4-(Trifluoromethoxy)benzene-1,2-diamine
[0227] Quinoline-7-carboxylic acid (34.6 mg, 0.2 mmol, 1.0 equiv) and 4- trifluoromethoxy-l,2-diaminobenzene (40.3 mg, 0.21 mmol, 1.05 equiv) were suspended in dry Nu,Nu-dimethyl formamide (0.17 M) under argon atmosphere followed by the addition of triethylamine (1.2 equiv). Then HATU (N-[(Dimethylamino)-lH-l,2,3-triazolo-[4,5-b]pyridin-l- ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide) (1.2 equiv) was added and the reaction mixture was stirred for 16 hours at room temperature. After dilution with water, the mixture was extracted with dichloromethane (3 x 20 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on C18-silica gel (water/acetonitrile + 0.1% trifluoroacetic acid). Fractions containing the desired product were combined and solvent was removed in vacuo. Solid product was dissolved in glacial acetic acid (0.2 M) and the resulting solution was heated in a sealed vial at 140 C for 2 hours. After cooling down to room temperature, acetic acid was removed in vacuo and the crude product was purified on C18-silica gel (water/acetonitrile + 0.1% trifluoroacetic acid). Fractions containing the desired product were combined and treated with saturated sodium bicarbonate solution. This mixture was extracted with dichloromethane (3 x 20 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 47.5 mg of the desired product 74 as an off-white solid (38% yield) in >95% purity as determined by HPLC. 1H NMR (500 MHz; CD30D): delta 8.95 (dd, J = 4.3, 1.5 Hz, 1H), 8.71 (s, 1H), 8.43 (d, J = 8.2 Hz, 1H), 8.35 (dd, J = 8.6, 1.7 Hz, 1H), 8.13 (d, J = 8.6 Hz, 1H), 7.71 (d, J = 8.9 Hz, 1H), 7.61 (dd, J (0637) (s, 1H), 7.24 (d, J= 8.8 Hz, 1H); LC/MS [m/z]: 330 [M+H]+.
The synthetic route of 4-(Trifluoromethoxy)benzene-1,2-diamine has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
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