(r)-Tert-butyl 1-(4-(5-carbamoyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate → (R)-4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

HRID 79519노트

반응식

HRID 79519 반응식
[C:1]([C:4]1[C:5]([N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:37])[C@H:20]([NH:29]C(=O)OC(C)(C)C)[CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:15][CH2:14]2)=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)(=O)[NH2:2]>O=P(Cl)(Cl)Cl>[NH2:29][C@H:20]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)[C:19]([N:16]1[CH2:17][CH2:18][N:13]([C:5]2[C:4]([C:1]#[N:2])=[CH:9][N:8]=[C:7]3[NH:10][CH:11]=[CH:12][C:6]=23)[CH2:14][CH2:15]1)=[O:37]

참가 물질

3

반응물 1

HCID 68761929(r)-Tert-butyl 1-(4-(5-carbamoyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate

생성물 1

HCID 44198751(R)-4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile수율 7.4%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

반응 조건

온도
70 °C

실험 절차

(R)-tert-Butyl 1-(4-(5-carbamoyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate (0.035 g, 0.066 mmol) was placed in POCl3 (2 mL) and heated to 70° C. for 2 hours. The reaction was then concentrated, diluted with DCM, and washed with saturated NaHCO3. The organic fraction was dried, filtered and concentrated to give a crude residue. The residue was purified (SP4, 12+M, water/CAN 95/5→60/40, 20CV) to give (R)-4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (0.002 g, 7.4% yield). MS ESI (+) m/z 409 detected.

후처리

  1. concentrationThe reaction was then concentrated
  2. additiondiluted with DCM
  3. washwashed with saturated NaHCO3
  4. customThe organic fraction was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude residue
  8. customThe residue was purified (SP4, 12+M, water/CAN 95/5→60/40, 20CV)

출처 및 근거

ORD 기록
ord-674da9d08c5d42b79b70932db553a418
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

반응 노트

불러오는 중…