Acetic Acid → 4-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide

HRID 912661

반응식

HRID 912661 반응식
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([NH2:9])=[O:8].[CH2:10]([C:14]1[NH:15][C:16]([Cl:21])=[C:17]([CH:19]=O)[N:18]=1)[CH2:11][CH2:12][CH3:13].[BH3-]C#N.[Na+].C(O)(=O)C>CO>[CH2:10]([C:14]1[NH:18][C:17]([CH2:19][NH:1][C:2]2[N:3]=[CH:4][NH:5][C:6]=2[C:7]([NH2:9])=[O:8])=[C:16]([Cl:21])[N:15]=1)[CH2:11][CH2:12][CH3:13]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 96795-Aminoimidazole-4-carboxamideHCID 551762-Butyl-5-chloro-1H-imidazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 674141614-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide수율 26%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A reaction mixture of 4-amino-5-imidazolecarboxamide (0.50 g, 3.96 mmol), 2-butyl-5-chloro-1H-imidazole-4-carbaldehyde (0.89 g, 4.76 mmol), and NaCNBH3 (0.25 g, 3.96 mmol) in methanol (5 mL) was stirred at r.t. over night. Acetic acid (0.24 g, 3.96 mmol) was added and the mixture was heated at 50° C. for 5 h. The mixture was concentrated in vacuo and dissolved in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate. 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 0.30 g (26%) of the title compound.

후처리

  1. temperaturethe mixture was heated at 50° C. for 5 h
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol)

출처 및 근거

ORD 기록
ord-ef92e652f2bb4a359c25e63cdfca4f47
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026244B2

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