Acetic Acid → Ethyl 3-{[(4,5-dimethyl-1H-benzimidazol-2-yl)methyl]amino}-1H-pyrrole-2-carboxylate

HRID 1171794ノート

反応式

HRID 1171794 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[NH2:11])=[O:5])[CH3:2].[CH3:12][C:13]1[C:21]2[N:20]=[C:19]([CH:22]=O)[NH:18][C:17]=2[CH:16]=[CH:15][C:14]=1[CH3:24].CC(O)=O.[BH3-]C#N.[Na+].[OH-].[Na+]>CO>[CH3:12][C:13]1[C:21]2[N:20]=[C:19]([CH2:22][NH:11][C:10]3[CH:9]=[CH:8][NH:7][C:6]=3[C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:18][C:17]=2[CH:16]=[CH:15][C:14]=1[CH3:24]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 451207614,5-Dimethyl-1H-benzo[d]imidazole-2-carbaldehyde

生成物 1

HCID 67068491Ethyl 3-{[(4,5-dimethyl-1H-benzimidazol-2-yl)methyl]amino}-1H-pyrrole-2-carboxylate収率 27.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3-Amino-1H-pyrrole-2-carboxylic acid ethyl ester (0.077 g, 0.5 mmol), 4,5-dimethyl-1H-benzimidazole-2-carbaldehyde (0.130 g, 0.75 mmol) and HOAc (0.045 g, 0.75 mmol) were stirred in methanol (4 mL) followed by addition of NaCNBH3. The resulting mixture was stirred at r.t. for 16 h. The reaction mixture was neutralized with 2M NaOH and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and extracted with water. The organic layer was dried (Na2SO4) and concentrated. The crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 100% ethyl acetate), obtaining a white solid, 0.043 g (27%) of the title compound, as a tautomeric mixture (1:1).

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. extractionextracted with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 100% ethyl acetate)

出典と根拠

ORDレコード
ord-1b6e509cf8be414480804c56d951eeac
出典データセット
uspto-grants-2010_11
特許番号
US07829707B2

反応ノート

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