Sodium bis(trimethylsilyl)amide → N-cyclohexyl-N-methyl-4-(1H-imidazo[4,5-c]pyridinylmethyl)benzamide

HRID 1034287ノート

反応式

HRID 1034287 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[NH:11]1[C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N:13]=[CH:12]1.[CH:20]1([N:26]([CH3:37])[C:27](=[O:36])[C:28]2[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1COCC1.C(OCC)(=O)C.CO.O>[CH:20]1([N:26]([CH3:37])[C:27](=[O:36])[C:28]2[CH:33]=[CH:32][C:31]([CH2:34][N:11]3[C:19]4[CH:18]=[CH:17][N:16]=[CH:15][C:14]=4[N:13]=[CH:12]3)=[CH:30][CH:29]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

参加物

8

反応物 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 14797401N-cyclohexyl-N-methyl-4-bromomethylbenzamideHCID 178419860HCID 178419860、化合物

生成物 1

HCID 14369772N-cyclohexyl-N-methyl-4-(1H-imidazo[4,5-c]pyridinylmethyl)benzamide収率 5.6%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium bis(trimethylsilyl)amide (22 ml of 1M solution in THF) was added to a stirred solution of imidazo(4,5-c]pyridine (2.60 g, 0.02 mol) in dry TEF (200 ml) under-argon. A fine white precipitate formed. After 90 m the mixture was treated with purified N-cyclohexyl-N-methyl 4-bromomethylbenzamide (6.20 g, 0.02 mol) dissolved in dry THF (50 ml). The mixture was allowed to warm to ambient temperature and stirred overnight. Methanol (1 ml) was added, followed by water and the product extracted using ethyl acetate (3×150 ml). The combined organic layers were washed with water (2×100 ml), dried over K2CO3 and the solvent removed to give the crude product. Flash chromatography (flash silica, 10% methanol in ethyl acetate) followed by repeated fractional crystallisation (6 times from ethyl acetate/DIPE) gave the desired regioisomer N-cyclohexyl-N-methyl 4-(1H-imidazo(4,5-c]pyridin-1-ylmethyl)benzamide (0.39 g, 5%) as an off white crystalline solid.

後処理

  1. customA fine white precipitate formed
  2. extractionthe product extracted
  3. washThe combined organic layers were washed with water (2×100 ml)
  4. dry with materialdried over K2CO3
  5. customthe solvent removed
  6. customto give the crude product
  7. customcrystallisation (6 times from ethyl acetate/DIPE)

出典と根拠

ORDレコード
ord-591e4c5f66734757b8896f1c4db6cbab
出典データセット
uspto-grants-1994_05
特許番号
US05314880

反応ノート

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