Water → tert-butyl N-[(3S)-1-[3-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-3-piperidyl]carbamate

HRID 57941노트

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HRID 57941 반응식
Cl[C:2]1[C:3]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25]2)=[N:4][C:5]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:6][N:7]=1.[CH3:38]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Na+].[Na+].O>C(#N)C.C([O-])(=O)C.[K+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH3:38][C:2]1[C:3]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25]2)=[N:4][C:5]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:6][N:7]=1

참가 물질

8

반응물 4

HCID 962Water2회HCID 10340Sodium CarbonateHCID 574072TrimethylboroxineHCID 86707120tert-butyl N-[(3S)-1-[3-chloro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-3-piperidyl]carbamate

생성물 1

HCID 86707127tert-butyl N-[(3S)-1-[3-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-3-piperidyl]carbamate수율 70.6%

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 6342Acetonitrile용매HCID 517044Potassium Acetate용매

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온도
140 °C

실험 절차

To a solution of tert-butyl N-[(3S)-1-[3-chloro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-3-piperidyl]carbamate (50 mg, 0.096 mmol), trimethylboroxine (36 mg, 0.29 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (8.0 mg, 0.0095 mmol) in acetonitrile 2.0 mL was added 1.00M sodium carbonate in water (0.19 mL, 0.19 mmol) and 1.00M potassium acetate in Water (0.19 mL, 0.19 mmol). The reaction mixture was heated in microwave at 140° C. for 40 min. The reaction was filtered through celite. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 80% EtOAc) to give the desired product 34 mg 70% yield. MS (ESI) m/z: 502.2.

후처리

  1. filtrationThe reaction was filtered through celite
  2. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 80% EtOAc)

출처 및 근거

ORD 기록
ord-103a7dba019443c980fb64f877f27d94
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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