Acetonitrile → 2-(3-(4-(7-(1-isopropyl-1-H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoro ethyl)azetidin-3-yl)acetonitrile

HRID 1853026Notes

Reaction equation

HRID 1853026 reaction equation
Cl.[CH:2]([N:5]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[N:18][N:19]([C:21]4([CH2:25][C:26]#[N:27])[CH2:24][NH:23][CH2:22]4)[CH:20]=3)[N:13]3[CH:28]=[CH:29][N:30]=[C:12]3[CH:11]=2)[CH:7]=[N:6]1)([CH3:4])[CH3:3].C(#N)C.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:46][C:47]([F:50])([F:49])[F:48])(=O)=O>C(Cl)Cl>[CH:2]([N:5]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[N:18][N:19]([C:21]4([CH2:25][C:26]#[N:27])[CH2:22][N:23]([CH2:46][C:47]([F:50])([F:49])[F:48])[CH2:24]4)[CH:20]=3)[N:13]3[CH:28]=[CH:29][N:30]=[C:12]3[CH:11]=2)[CH:7]=[N:6]1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 674569432-(3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride

Product 1

HCID 682307732-(3-(4-(7-(1-isopropyl-1-H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoro ethyl)azetidin-3-yl)acetonitrileYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with 2-(3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (0.050 g, 0.10 mmol) was added 1 mL of acetonitrile, potassium carbonate (0.10 g, 0.75 mmol), and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.040 g, 0.17 mmol) at ambient temperature with stirring. The reaction flask was then sealed and allowed to proceed at ambient temperature over the weekend. The reaction was diluted with DCM and the suspension was loaded directly onto a silica gel column pre-wetted and eluted with 75% ethyl acetate in Hexanes with 1% ammonium hydroxide to afford the title compound (0.022 g, 0.047 mmol, 47% yield). MS (apci) m/z=470.2 (M+H).

Workup

  1. customThe reaction flask was then sealed
  2. customto proceed at ambient temperature over the weekend
  3. washeluted with 75% ethyl acetate in Hexanes with 1% ammonium hydroxide

Sources & evidence

ORD record
ord-ccd7bc7b820640f4929930832e8b2363
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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