Benzoyl isothiocyanate → 4-{[(benzoylamino)carbonothioyl][(2-butyl-4-chloro-1H-imidazol-5-yl)methlyl]amino}-1H-imidazole-5-carboxamide

HRID 912662노트

반응식

HRID 912662 반응식
[CH2:1]([C:5]1[NH:6][C:7]([CH2:11][NH:12][C:13]2[N:14]=[CH:15][NH:16][C:17]=2[C:18]([NH2:20])=[O:19])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:21]([N:29]=[C:30]=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.CO>[C:21]([NH:29][C:30]([CH:11]([NH:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([NH2:20])=[O:19])[C:7]1[NH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][C:8]=1[Cl:10])=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 2

HCID 68284Benzoyl isothiocyanateHCID 674141614-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide

생성물 1

HCID 1317291954-{[(benzoylamino)carbonothioyl][(2-butyl-4-chloro-1H-imidazol-5-yl)methlyl]amino}-1H-imidazole-5-carboxamide수율 38%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

4-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide (0.30 g, 1.01 mmol, obtained from Example 7(a)) was dissolved in CH2Cl2 (5 mL) and methanol (2 mL). Benzoylisothiocyanate (0.18 g, 1.11 mmol) was added and the mixture was stirred at r.t. for 4 h. The mixture was then concentrated in vacuo and dissolved in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol), obtaining 0.175 g (38%) of the title compound. MS (ESI) m/z 460 (M+1).

후처리

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol)

출처 및 근거

ORD 기록
ord-1a9c1ad27aa14b9cb4ccd4b515516c50
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026244B2

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