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 57941ノート

反応式

HRID 57941 の反応式
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

参加物

8

反応物 4

HCID 962Water2 回HCID 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

生成物 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]carbamate収率 70.6%

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 6342Acetonitrile溶媒HCID 517044Potassium Acetate溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-103a7dba019443c980fb64f877f27d94
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

反応ノート

読み込み中…