Acrylamide → 1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indole

HRID 728598

反応式

HRID 728598 の反応式
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[C:21]([NH2:25])(=[O:24])[CH:22]=[CH2:23].[Cl-].[NH4+]>CN(C)C=O>[C:21]([CH2:22][CH2:23][N:15]1[C:16]2[C:12](=[CH:11][C:10]([C:8](=[O:9])[NH:7][CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:18][CH:17]=2)[CH:13]=[CH:14]1)(=[O:24])[NH2:25]

参加物

6

反応物 4

HCID 6579AcrylamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 100373961h-Indole-5-carboxamide,n-(cyclopentylmethyl)-

生成物 1

HCID 198224771-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indole収率 36.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of 5-(N-cyclopentylmethylcarbamoyl)indole (A) (1.50 g) in N,N-dimethylformamide (DMF) (5 ml) was added to a stirred slurry of sodium hydride (0.16 g) in DMF (15 ml) maintained at 0° C. under an atmosphere of nitrogen. The mixture was warmed to room temperature for 15 minutes, treated with a solution of acrylamide (0.66 g) in DMF (5 ml), and allowed to stir for 12 hours. The mixture was poured into a cold, saturated aqueous solution of ammonium chloride to give a milky suspension which was extracted with ethyl acetate. The organic phase was washed successively with water and brine, dried (MgSO4), and evaporated. The resulting clear oil was purified by flash chromatography on silica gel (700 ml), eluting with 7:93 v/v methanol:ethyl acetate, to give 1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indole (0.70 g, 36%) as a gummy white foam; NMR (80 MHz, CDCl3): 1.2-2.2(broad m, 9H, cyclopentyl), 2.7(t, 2H, CH2CO), 3.4(dd, 2H, CH2NH), 4.5(t, 2H, CH2CH2CO), 5.4(broad, 2H, CONH2), 6.5(dd, 1H, H3 -indole), 7.2(d, 1H2 -indole), 7.3(d, 1H, H7 -indole), 7.6(dd, 1H, H6 -indole), 8.0(m, 1H, H4 -indole).

後処理

  1. temperatureThe mixture was warmed to room temperature for 15 minutes
  2. customto give a milky suspension which
  3. extractionwas extracted with ethyl acetate
  4. washThe organic phase was washed successively with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe resulting clear oil was purified by flash chromatography on silica gel (700 ml)
  8. washeluting with 7:93 v/v methanol

出典と根拠

ORDレコード
ord-7ce83e70e4f9432386bd9fe1e473dcb0
出典データセット
uspto-grants-1991_09
特許番号
US05049576

関連ノート

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