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Cyanoacetic acid → 3-[2-[[4-Amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]azetidin-1-yl]-3-oxo-propanenitrile

HRID 1778440
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인쇄 미리보기

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HRID 1778440 반응식
[NH:1]1[CH2:4][CH2:3][CH:2]1[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[N:13][C:14]([NH2:15])=[C:9]2[C:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][C:17]=2[F:29])=[N:7]1.[C:30]([CH2:32][C:33](O)=[O:34])#[N:31].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)Cl>[NH2:15][C:14]1[N:13]=[CH:12][N:11]=[C:10]2[N:6]([CH2:5][CH:2]3[CH2:3][CH2:4][N:1]3[C:33](=[O:34])[CH2:32][C:30]#[N:31])[N:7]=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:18][C:17]=3[F:29])[C:9]=12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 9740Cyanoacetic acidHCID 111923Propylphosphonic anhydrideHCID 900012121-(Azetidin-2-ylmethyl)-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-4-amine

생성물 1

HCID 900011903-[2-[[4-Amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]azetidin-1-yl]-3-oxo-propanenitrile수율 72%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a mixture of 1-(azetidin-2-ylmethyl)-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-4-amine (236.4 mg, 0.610 mmol), 2-cyanoacetic acid (77.2 mg, 0.910 mmol) in DCM (8 mL) in ice bath, was added T3P (0.36 mL, 1.21 mmol) and TEA (0.34 mL, 2.42 mmol). The ice bath was removed and the reaction mixture was stirred at room temperature overnight. The reaction mixture was loaded onto the silica gel column, purified with 0-3% gradient MeOH:CH2CL2, to get 3-[2-[[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]azetidin-1-yl]-3-oxo-propanenitrile (201 mg) as yellow oil.

후처리

  1. customThe ice bath was removed
  2. custompurified with 0-3% gradient MeOH

출처 및 근거

ORD 기록
ord-541a246e141a4de48a9a9befb3fdd9ac
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266895B2

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