Acetaldehyde → 2-(2-(2-(2-((1-(1-Ethylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592469노트

반응식

HRID 592469 반응식
[CH:1](=O)[CH3:2].[NH:4]1[CH2:9][CH2:8][CH:7]([N:10]2[CH:14]=[C:13]([NH:15][C:16]3[N:21]=[C:20]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH:30]([CH3:34])[C:31]([NH2:33])=[O:32])[C:19]([C:35]([F:38])([F:37])[F:36])=[CH:18][N:17]=3)[CH:12]=[N:11]2)[CH2:6][CH2:5]1>CCO>[CH2:1]([N:4]1[CH2:5][CH2:6][CH:7]([N:10]2[CH:14]=[C:13]([NH:15][C:16]3[N:21]=[C:20]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH:30]([CH3:34])[C:31]([NH2:33])=[O:32])[C:19]([C:35]([F:37])([F:36])[F:38])=[CH:18][N:17]=3)[CH:12]=[N:11]2)[CH2:8][CH2:9]1)[CH3:2]

참가 물질

4

반응물 2

HCID 177AcetaldehydeHCID 732951232-(2-(2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-ylethyl)phenyl)propanamide

생성물 1

HCID 732952942-(2-(2-(2-((1-(1-Ethylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide수율 79%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Acetaldehyde (17 μL, 0.31 mmol) was added to a solution of 2-(2-(2-(2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide A67 (50 mg, 0.10 mmol) in EtOH (20 mL). After 10 minutes, NaHB(OAc)3 (86 mg, 0.41 mmol) was added and the mixture was stirred for 3 hours. The reaction was quenched with water (20 mL) and the volatiles were removed in vacuo. The resultant solid was suspended in water (25 mL), sonicated for 10 minutes, collected by filtration and then dissolved in acetone (3 mL). Addition of petroleum benzine 40-60° C. gave a precipitate that was collected by filtration to give the title compound 59 as a tan solid (42 mg, 79%). LCMS-A: rt 4.808 min; m/z 516.3 [M+H]+.

후처리

  1. customThe reaction was quenched with water (20 mL)
  2. customthe volatiles were removed in vacuo
  3. customsonicated for 10 minutes
  4. filtrationcollected by filtration
  5. dissolutiondissolved in acetone (3 mL)
  6. additionAddition of petroleum benzine 40-60° C.
  7. customgave a precipitate that
  8. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-18b95dae3afe454b9d120a1e66567a49
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238644B2

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