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

HRID 1197659노트

반응식

HRID 1197659 반응식
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

참가 물질

8

반응물 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 14797401N-cyclohexyl-N-methyl-4-bromomethylbenzamideHCID 178419860HCID 178419860, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 887Methanol용매2회HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b036e55eb3c64136ba76b25923749624
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05276153

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