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

HRID 548781ノート

反応式

HRID 548781 の反応式
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]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 202206772-Methoxy-2-methylpropanal2 回HCID 178479549HCID 178479549、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f7aa78645d1843c5aef1d6b7347ca0a4
出典データセット
uspto-grants-2011_05
特許番号
US07943625B2

反応ノート

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