(2S)-2-(Trifluoromethyl)oxirane → HCID 44611358, compound

HRID 536381Notes

Reaction equation

HRID 536381 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:6]([CH3:15])=[CH:5][C:4]=1[NH:16][C:17]1[N:22]=[C:21]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)[C:20]([CH3:30])=[CH:19][N:18]=1.[F:31][C:32]([F:37])([F:36])[C@@H:33]1[CH2:35][O:34]1>CN(C=O)C>[CH3:15][C:6]1[CH:5]=[C:4]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=3)[C:20]([CH3:30])=[CH:19][N:18]=2)[C:3]([CH3:2])=[CH:8][C:7]=1[CH:9]1[CH2:14][CH2:13][N:12]([CH2:35][C@H:33]([OH:34])[C:32]([F:37])([F:36])[F:31])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 7171781(2S)-2-(Trifluoromethyl)oxiraneHCID 86653271HCID 86653271, compound

Product 1

HCID 44611358HCID 44611358, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N2-(2,5-dimethyl-4-(piperidin-4-yl)phenyl)-5-methyl-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine hydrochloride (36.0 mg, 0.084 mmol) in DMF (0.5 mL) were added TEA (23.4 μL, 0.168 mmol) and (S)-2-(trifluoromethyl)oxirane (72.8 μL, 0.84 mmol). The reaction mixture was stirred at room temperature overnight, and purified by preparative RP-HPLC to provide (S)-3-(4-(2,5-dimethyl-4-(5-methyl-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)phenyl)piperidin-1-yl)-1,1,1-trifluoropropan-2-ol; ESMS m/z 504.3 (M+H+).

Workup

  1. custompurified by preparative RP-HPLC

Sources & evidence

ORD record
ord-8eda16a2fc2849ccac4a6042ea17785f
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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