Triethylamine → 5-bromo-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

HRID 562030

반응식

HRID 562030 반응식
C(N(CC)CC)C.Cl.[Br:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([C:19]([NH2:21])=[O:20])[CH:18]=1)[NH:15][CH:14]=[C:13]2[CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[CH3:28][CH:29]([S:31](Cl)(=[O:33])=[O:32])[CH3:30]>CN(C=O)C.CCOC(C)=O.O>[Br:9][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([C:19]([NH2:21])=[O:20])[CH:18]=1)[NH:15][CH:14]=[C:13]2[CH:22]1[CH2:27][CH2:26][N:25]([S:31]([CH:29]([CH3:30])[CH3:28])(=[O:33])=[O:32])[CH2:24][CH2:23]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 667232845-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide hydrochloride

생성물 1

HCID 577326275-bromo-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide수율 75%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 22728543Water ethylacetate용매

실험 절차

Triethylamine (2.6 mL, 18.7 mmol) was added to a solution of 5-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide hydrochloride in DMF (15 mL) at 0° C. The mixture was stirred at room temperature for 10 min, and 2-propanesulfonyl chloride (1.04 mL, 9.32 mmol) was added. Stirring continued for another 30 min, and the reaction mixture was diluted with 1:1 EtOAc/H2O (200 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were washed with saturated NaCl (1×100 mL), dried (MgSO4), and concentrated under reduced pressure. The crude product was washed with MeOH (2×10 mL) to give the title compound (1.5 g, 75%).

후처리

  1. stirringStirring
  2. waitcontinued for another 30 min
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  5. washThe combined organic layers were washed with saturated NaCl (1×100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. washThe crude product was washed with MeOH (2×10 mL)

출처 및 근거

ORD 기록
ord-790a62cb8ee143c486885e2076fdd8d9
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063071B2

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