2,2,2-Trifluoroethyl trifluoromethanesulfonate → 2-(4-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoroethyl)piperidin-4-yl)acetonitrile

HRID 1852987Notes

Reaction equation

HRID 1852987 reaction equation
Cl.[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([C:19]4([CH2:25][C:26]#[N:27])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH:18]=3)[N:11]3[CH:28]=[CH:29][N:30]=[C:10]3[CH:9]=2)[CH:5]=[N:4]1.CCN(C(C)C)C(C)C.FC(F)(F)S(O[CH2:46][C:47]([F:50])([F:49])[F:48])(=O)=O>CN(C=O)C>[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([C:19]4([CH2:25][C:26]#[N:27])[CH2:20][CH2:21][N:22]([CH2:46][C:47]([F:50])([F:49])[F:48])[CH2:23][CH2:24]4)[CH:18]=3)[N:11]3[CH:28]=[CH:29][N:30]=[C:10]3[CH:9]=2)[CH:5]=[N:4]1

Participants

5

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 81531DiisopropylethylamineHCID 67456826HCID 67456826, compound

Product 1

HCID 674617692-(4-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoroethyl)piperidin-4-yl)acetonitrileYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidin-4-yl)acetonitrile hydrochloride (Example 28, Step A; 0.050 g, 0.11 mmol) was dissolved in DIEA (0.12 mL, 0.70 mmol) and DMF (0.2 mL) with sonication. 2,2,2-Trifluoroethyl trifluoromethanesulfonate (0.025 g, 0.11 mmol) was added and the reaction was stirred at ambient temperature. After four hours the reaction was applied to a silica caplet and pumped to dryness. The caplet was applied to a silica column and eluted with 0.5-2% MeOH/DCM. The purified product was isolated to provide 2-(4-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoroethyl)piperidin-4-yl)acetonitrile (5.0 mg, 10% yield) as a solid. MS (apci) m/z=470.2 (M+H).

Workup

  1. washeluted with 0.5-2% MeOH/DCM
  2. customThe purified product was isolated

Sources & evidence

ORD record
ord-1264ed0a77aa449eba16bf4294fc3f9e
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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