Acetic Acid → 4-[(2-methoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamide

HRID 548781노트

반응식

HRID 548781 반응식
Cl.[NH2:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]([NH2:10])=[O:9].[CH3:11][O:12][C:13]([CH3:17])([CH3:16])[CH:14]=O.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH3:11][O:12][C:13]([CH3:17])([CH3:16])[CH2:14][NH:2][C:3]1[N:7]=[CH:6][NH:5][C:4]=1[C:8]([NH2:10])=[O:9]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 202206772-Methoxy-2-methylpropanal2회HCID 178479549HCID 178479549, 화합물

생성물 1

HCID 671575204-[(2-methoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamide수율 73%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

5-Amino-4-imidazolecarboxamide hydrochloride (0.162 g, 1.0 mmol) and 2-methoxy-2-methylpropanal, which was obtained from Example 3(a) (0.204 g, 2.0 mmol) were mixed in methanol (3 mL) at r.t. Acetic acid (141 μL, 2.46 mmol) mL) was then added and the mixture was allowed to stir for 30 min followed by addition of NaCNBH3 (0.063 g, 1.0 mmol). After 3 h, additional 2-methoxy-2-methylpropanal (0.060 g, 0.59 mmol) was added. The reaction mixture was stirred at r.t. for 17 h and was then concentrated and purified by flash silica gel chromatography (CHCl3:MeOH=5:1). The title compound was obtained as an oil in 73% yield (0.155 g). MS (ESI) m/z 213 (M+1).

후처리

  1. waitAfter 3 h
  2. stirringThe reaction mixture was stirred at r.t. for 17 h
  3. concentrationwas then concentrated
  4. custompurified by flash silica gel chromatography (CHCl3:MeOH=5:1)

출처 및 근거

ORD 기록
ord-f7aa78645d1843c5aef1d6b7347ca0a4
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943625B2

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