[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea → [5-(3-Chloro-benzyl)-4-ethyl-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 604867

반응식

HRID 604867 반응식
Cl[CH:2]([C:11](=O)[CH2:12][CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[CH:5]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:29][C:30]([NH2:32])=[S:31])[CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1>>[Cl:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[CH2:3][C:2]1[S:31][C:30]([NH:29][C:19]2[CH:20]=[CH:21][C:22]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[C:17]([O:16][CH3:15])[CH:18]=2)=[N:32][C:11]=1[CH2:12][CH3:13]

참가 물질

3

반응물 2

HCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thioureaHCID 866246712-Chloro-1-(3-chloro-phenyl)-pentan-3-one

생성물 1

HCID 86624672[5-(3-Chloro-benzyl)-4-ethyl-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

실험 절차

The title compound was prepared in analogy to example 1 step e) from 76 mg (0.33 mmol) 2-chloro-1-(3-chloro-phenyl)-pentan-3-one and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 62 mg (47%) [5-(4-chloro-benzyl)-4-ethyl-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a light brown viscous oil. MS ISP (m/e): 439.2/441.2 (100/40) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.19 (s, 1H), 7.74 (s, 1H), 7.64 (s, 1H), 7.35-7.18 (m, 5H), 7.10 (d, 1H), 7.02 (s, 1H), 4.02 (s, 2H), 3.79 (s, 3H), 2.56 (q, 2H), 2.14 (s, 3H), 1.20 (t, 3H).

후처리

  1. customThe crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 62 mg (47%) [5-(4-chloro-benzyl)-4-ethyl-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a light brown viscous oil

출처 및 근거

ORD 기록
ord-0daf4cab85f94ca99697acfc94355a20
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910740B2

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