Diisopropylethylamine → N'-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-N'-isopropyl-hydrazine-carboxylic acid methyl ester

HRID 79867ノート

反応式

HRID 79867 の反応式
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[CH3:13][O:14][C:15]([NH:17][NH:18][CH:19]([CH3:21])[CH3:20])=[O:16].CCN(C(C)C)C(C)C.[Br:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[NH:42][C:41]([CH:43]3[CH2:47][CH2:46][CH2:45][NH:44]3)=[N:40][CH:39]=2)=[CH:34][CH:33]=1>C(Cl)Cl>[CH3:13][O:14][C:15]([NH:17][N:18]([C:5]([N:44]1[CH2:45][CH2:46][CH2:47][CH:43]1[C:41]1[NH:42][C:38]([C:35]2[CH:36]=[CH:37][C:32]([Br:31])=[CH:33][CH:34]=2)=[CH:39][N:40]=1)=[O:11])[CH:19]([CH3:21])[CH3:20])=[O:16]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 94429Triphosgene2 回HCID 436506945-(4-Bromo-phenyl)-2-pyrrolidin-2-yl-1H-imidazoleHCID 57863323Methyl 2-isopropylhydrazinecarboxylate

生成物 1

HCID 66621058N'-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-N'-isopropyl-hydrazine-carboxylic acid methyl ester収率 33.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Triphosgene (1.05 g) was dissolved in DCM (17 mL) and stirred at 0° C. N′-Isopropyl-hydrazine-carboxylic acid methyl ester (1.00 g) and DIPEA (1.5 mL) were dissolved in DCM (25 mL), and mixture was added to triphosgene solution and stirred for 10 minutes. 5-(4-Bromo-phenyl)-2-pyrrolidin-2-yl-1H-imidazole (2.65 g) was added. Reaction was stirred at room temperature for 1 hour and extracted twice with water (10 mL), once with brine (10 mL), and evaporated under vacuum. The resulting oil was subjected to silica gel chromatography using a 40 g ISCO column and effluent of 0-100% ethyl acetate:hexanes. The fractions containing product were combined and the solvent was removed under vacuum, giving N′-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-N′-isopropyl-hydrazine-carboxylic acid methyl ester (533 mg, 16%).

後処理

  1. stirringstirred for 10 minutes
  2. customReaction
  3. stirringwas stirred at room temperature for 1 hour
  4. extractionextracted twice with water (10 mL), once with brine (10 mL)
  5. customevaporated under vacuum
  6. additionThe fractions containing product
  7. customthe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-1c312cfcea424c209384ee2b6b297e54
出典データセット
uspto-grants-2014_09
特許番号
US08841278B2

反応ノート

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