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

HRID 1197659ノート

反応式

HRID 1197659 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2 回HCID 8857Ethyl Acetate溶媒

実験手順

Sodium bis(trimethylsilyl)amide (22 ml of 1 M solution in THF) was added to a stirred solution of imidazo[4,5-c]pyridine (2.60 g, 0.02 mol) in dry THF (200 ml) under argon. A fine white precipitate formed. After 90 min. the mixture was treated with 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 anhydrous potassium carbonate 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-(1 H-imidazo[4,5-c]pyridylmethyl)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. washwere washed
  4. dry with materialwith water (2×100 ml), dried over anhydrous potassium carbonate
  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-b036e55eb3c64136ba76b25923749624
出典データセット
uspto-grants-1994_01
特許番号
US05276153

反応ノート

読み込み中…