2-(Trifluoromethyl)oxirane → 3-(4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)naphthalen-1-yl)piperidin-1-yl)-1,1,1-trifluoropropan-2-ol

HRID 2093823Notes

Reaction equation

HRID 2093823 reaction equation
[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=2)=[N:4][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[F:32][C:33]([F:38])([F:37])[CH:34]1[CH2:36][O:35]1>CN(C=O)C>[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=2)=[N:4][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:36][CH:34]([OH:35])[C:33]([F:38])([F:37])[F:32])[CH2:21][CH2:20]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 5207692-(Trifluoromethyl)oxiraneHCID 582571215-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-(piperidin-4-yl)naphthalene-1-yl)pyrimidine-2,4-diamine

Product 1

HCID 582571233-(4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)naphthalen-1-yl)piperidin-1-yl)-1,1,1-trifluoropropan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-(piperidin-4-yl)naphthalene-1-yl)pyrimidine-2,4-diamine (30.8 mg, 0.07 mmol) and 2-(trifluoromethyl)oxirane (39.2 mg, 0.35 mmol) in 1 mL of DMF was stirred at room temperature overnight. The crude mixture was purified by RP-HPLC to give 3-(4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)naphthalen-1-yl)piperidin-1-yl)-1,1,1-trifluoropropan-2-ol; ESMS m/z 546.2 (M+H+).

Workup

  1. customThe crude mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-7739efdb3422411687ae6a52e3487a2e
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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