2-(4-Chlorophenyl)-2-oxoethyl thiocyanate → [4-(4-Chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 604875노트

반응식

HRID 604875 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH2:24][S:25][C:26]#[N:27])=[CH:19][CH:18]=1>C(O)C.O1CCOCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:27]=[C:26]([NH:15][C:5]3[CH:6]=[CH:7][C:8]([N:9]4[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[S:25][CH:24]=2)=[CH:19][CH:18]=1

참가 물질

5

반응물 2

HCID 880132-(4-Chlorophenyl)-2-oxoethyl thiocyanateHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

생성물 1

HCID 86624674[4-(4-Chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

시약·촉매·용매 2

HCID 702Ethanol용매HCID 312751,4-Dioxane용매

실험 절차

A solution of 51 mg (0.25 mmol) 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine and of 53 mg (0.25 mmol) 1-(4-chloro-phenyl)-2-thiocyanato-ethanone in ethanol (1.25 ml) and dioxane (1.25 ml) was refluxed over night. After cooling to room temperature the solvent was evaporated under vacuo and the residue was purified on silica gel with methylene chloride/methanol 19/1 yielding 35 mg (35%) [4-(4-chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a yellow solid. MS ISP (m/e): 397.1/399.1 (100/50) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.54 (s, 1H), 7.96 (d, 2H), 7.86 (s, 1H), 7.68 (s, 1H), 7.50 (d, 2H), 7.48 (s, 1H), 7.31 (d, 1H), 7.22 (d, 1H), 7.06 (s, 1H).

후처리

  1. customwas evaporated under vacuo
  2. customthe residue was purified on silica gel with methylene chloride/methanol 19/1 yielding 35 mg (35%) [4-(4-chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a yellow solid

출처 및 근거

ORD 기록
ord-ff47168e96584356b0921843bccb64bb
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910740B2

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