1-Isothiocyanato-3-(trifluoromethyl)benzene → 1-(2-Phenyl-1,1-bis(3-(trifluoromethoxy)phenyl)ethyl)-3-(3-(trifluoromethyl)phenyl)thiourea

HRID 238797

반응식

HRID 238797 반응식
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:5]=[C:6]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[NH2:11])[CH:7]=[CH:8][CH:9]=1.[N:25]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1)=[C:26]=[S:27]>C(Cl)Cl>[C:6]1([CH2:10][C:10]([NH:11][C:26]([NH:25][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:37])[F:36])[CH:29]=2)=[S:27])([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:20])[F:21])[CH:13]=2)[C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:23])([F:24])[F:1])[CH:5]=2)[CH:7]=[CH:8][CH:9]=[CH:4][CH:5]=1

참가 물질

4

반응물 2

HCID 1372321-Isothiocyanato-3-(trifluoromethyl)benzeneHCID 86613053Bis(3-(trifluoromethoxy)phenyl)methanamine

생성물 1

HCID 235820971-(2-Phenyl-1,1-bis(3-(trifluoromethoxy)phenyl)ethyl)-3-(3-(trifluoromethyl)phenyl)thiourea

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of bis(3-(trifluoromethoxy)phenyl)methanamine (20 mg, 0.057 mmol) in CH2Cl2 (0.1 mL) was added 1-isothiocyanato-3-(trifluoromethyl)benzene (35 mg, 0.17 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was concentrated and the residue was purified by prep HPLC (phenomenex AXIA Luna 75×30 mm, 5μ column eluting with 10-90% ACN/H2O over 10 minutes containing 0.1% TFA; 40 mL/min, monitoring at 220 nm) to afford 1-(2-phenyl-1,1-bis(3-(trifluoromethoxy)phenyl)ethyl)-3-(3-(trifluoromethyl)phenyl)thiourea (Example 284) as white lyophillate (30 mg, 81%). LCMS: RT=4.51 min [M+H] 645.14 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by prep HPLC (phenomenex AXIA Luna 75×30 mm, 5μ column eluting with 10-90% ACN/H2O over 10 minutes containing 0.1% TFA; 40 mL/min, monitoring at 220 nm)

출처 및 근거

ORD 기록
ord-e790ee04723a40e796890ae32d156ac5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642576B2

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