Methyl iodide → Methyl 4-[(5-chloro-2-{[4-(trifluoromethoxy)-phenyl]amino}-1H-benzimid-azol-1-yl)methyl]benzoate

HRID 1594514노트

반응식

HRID 1594514 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.[F:21][C:22]([F:34])([F:33])[O:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=S)=[CH:26][CH:25]=1.CI.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH2:10][C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)[C:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([O:23][C:22]([F:21])([F:33])[F:34])=[CH:25][CH:26]=3)=[N:1][C:2]=2[CH:7]=1

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 27773384-(Trifluoromethoxy)phenyl isothiocyanateHCID 68996953Methyl 4-{[(2-amino-4-chlorophenyl)amino]methyl}benzoate

생성물 1

HCID 69442168Methyl 4-[(5-chloro-2-{[4-(trifluoromethoxy)-phenyl]amino}-1H-benzimid-azol-1-yl)methyl]benzoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

The title compound of Example 12, Step B (0.5 mmol, 145 mg) and 4-trifluoromethoxyphenyl isothiocyanate (0.5 mmol, 81 μL) were heated in DCM (1 mL) for 1 h, then allowed to stand at ambient temperature for 16 h. MeI (1.0 mmol, 62 μL), DIEA (1.0 mmol, 174 μL) and DMF (0.5 mL) were added and the solution was heated at 40° C. for 2 h. The reaction mixture was partitioned between EtOAc/brine and the organic phase was dried with Na2SO4 and concentrated in vacuo. Flash chromatography on silica eluting with 18% EtOAc in hexanes afforded the product as a beige solid. LC-MS (ESI, Method C): 3.85 min, m/z 476.1 (M+1).

후처리

  1. customThe reaction mixture was partitioned between EtOAc/brine
  2. dry with materialthe organic phase was dried with Na2SO4
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-84f56c1863d2409fbb13a586d18fe6fa
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07301036B2

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