Trimethyl-(6-methylpyrazin-2-yl)stannane → tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-2-oxo-3-piperidyl]carbamate

HRID 57933노트

반응식

HRID 57933 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:18]4=[O:31])[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C[Sn](C)(C)[C:34]1[CH:39]=[N:38][CH:37]=[C:36]([CH3:40])[N:35]=1>CN(C)C(=O)C>[CH3:40][C:36]1[N:35]=[C:34]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[N:16]=[C:15]([N:17]5[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28])[C:18]5=[O:31])[CH:14]=[CH:13][CH:12]=4)[C:4]=3[CH:3]=2)[CH:39]=[N:38][CH:37]=1

참가 물질

4

반응물 2

HCID 86707041Trimethyl-(6-methylpyrazin-2-yl)stannaneHCID 86707118tert-butyl N-[(3S)-1-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-2-oxo-3-piperidyl]carbamate

생성물 1

HCID 86707119tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-2-oxo-3-piperidyl]carbamate

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
145 °C

실험 절차

A solution of tert-butyl N-[(3S)-1-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-2-oxo-3-piperidyl]carbamate (125 mg, 0.282 mmol) and palladium(0)tetrakis(triphenylphosphine) (32 mg, 0.028 mmol) in N,N-dimethylacetamide 5.0 mL was added trimethyl-(6-methylpyrazin-2-yl)stannane (145 mg, 0.565 mmol). The reaction mixture heated at 145° C. for 40 min in CEM microwave. The reaction mixture was filtered through celite and concentrated. The crude product was diluted with EtOAc then washed with water. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was carried to next step. MS (ESI) m/z: 501.1.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. additionThe crude product was diluted with EtOAc
  4. washthen washed with water
  5. dry with materialThe organic layers was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-acdb07c56cad45f7b3de64efa2089dd7
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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