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

HRID 592469ノート

反応式

HRID 592469 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-18b95dae3afe454b9d120a1e66567a49
出典データセット
uspto-grants-2016_01
特許番号
US09238644B2

反応ノート

読み込み中…