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

HRID 728675

반응식

HRID 728675 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
0 °C

실험 절차

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, 1H, H2 -indole), 7.3(d, 1H, H7 -indole), 7.6(dd, 1H, H6 -indole), 8.0(m, 1H, H4 -indole).

후처리

  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

출처 및 근거

ORD 기록
ord-8b05121848f94a8bba8f79c029c9c427
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05049679

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