Water → (R)-tert-Butyl 1-(4-(5-bromo-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate

HRID 79512노트

반응식

HRID 79512 반응식
Cl.Cl.[Br:3][C:4]1[C:5]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1.[C:19]([O:23][C:24]([NH:26][C@H:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:28](O)=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20].ON1C2C=CC=CC=2N=N1.O.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>C(Cl)Cl>[Br:3][C:4]1[C:5]([N:13]2[CH2:18][CH2:17][N:16]([C:28](=[O:29])[C@H:27]([NH:26][C:24](=[O:25])[O:23][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:31][C:32]3[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=3)[CH2:15][CH2:14]2)=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1

참가 물질

8

반응물 6

HCID 962WaterHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 687629915-Bromo-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochloride

생성물 1

HCID 68763825(R)-tert-Butyl 1-(4-(5-bromo-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate수율 63.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-Bromo-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochloride (0.20 g, 0.56 mmol) and (R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (0.677 g, 2.25 mmol) were placed in DCM (5 mL) at room temperature. 1-Hydroxybenzotriazole (“HOBT”)—H2O (0.121 g, 0.79 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (“EDCI”; 0.14 g, 0.73 mmol), and triethylamine (0.39 mL, 2.82 mmol) were then added, and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with saturated Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, and concentrated to give a crude residue. The crude residue was purified by column chromatography (500:7 DCM:MeOH) to give (R)-tert-butyl 1-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate (0.20 g, 62.9% yield).

후처리

  1. customThe reaction was then quenched with saturated Na2CO3
  2. extractionextracted with DCM
  3. customThe combined organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude residue
  7. customThe crude residue was purified by column chromatography (500:7 DCM:MeOH)

출처 및 근거

ORD 기록
ord-6a5dc7fd30484519a51273a6e0fc1bf0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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