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

HRID 592469Notes

Reaction equation

HRID 592469 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-18b95dae3afe454b9d120a1e66567a49
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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