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tert-Butyl 4-(4-((4-((2-(1-amino-1-oxopropan-2-yl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate → tert-Butyl 4-(4-((4-(2-(1-amino-1-oxopropan-2-yl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate

HRID 592465
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HRID 592465 반응식
[NH2:1][C:2](=[O:42])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[C:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]2[CH:25]=[N:26][N:27]([CH:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]3)[CH:28]=2)[N:14]=1)[CH3:4]>CN(C=O)C.[Pd]>[NH2:1][C:2](=[O:42])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]2[CH:25]=[N:26][N:27]([CH:29]3[CH2:30][CH2:31][N:32]([C:35]([O:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36])[CH2:33][CH2:34]3)[CH:28]=2)[N:14]=1)[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 1

HCID 86712338tert-Butyl 4-(4-((4-((2-(1-amino-1-oxopropan-2-yl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate

생성물 1

HCID 86712339tert-Butyl 4-(4-((4-(2-(1-amino-1-oxopropan-2-yl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of tert-butyl 4-(4-((4-((2-(1-amino-1-oxopropan-2-yl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate A65 (3.30 g, 5.66 mmol) in DMF (50 mL) and TEA (5 mL) was stirred with 10% Pd/C (wetted with ca. 53% water, 3.00 g) under an atmosphere of H2 for 20 hours at 35° C. The mixture was filtered through Celite and the solvent was removed in vacuo. Purification by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 20-100% EtOAc in petroleum benzine 40-60° C.) gave the title compound A66 as a yellow solid (3.32 g, 99%). LCMS-D: rt 3.54 min; m/z 588 [M+H]+.

후처리

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent was removed in vacuo
  3. customPurification by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 20-100% EtOAc in petroleum benzine 40-60° C.)

출처 및 근거

ORD 기록
ord-099bf9820c064285b04eeb9cf4ad221e
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238644B2

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