Acetonitrile → HCID 67456817, compound

HRID 1853071Notes

Reaction equation

HRID 1853071 reaction equation
Cl.Cl.Cl.[CH:4]1([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([C:18]4([CH2:22][C:23]#[N:24])[CH2:21][NH:20][CH2:19]4)[CH:17]=3)[N:10]3[CH:25]=[CH:26][N:27]=[C:9]3[CH:8]=2)[CH2:6][CH2:5]1.C(#N)C.FC(F)(F)S(O[CH2:37][C:38]([F:41])([F:40])[F:39])(=O)=O>O>[CH:4]1([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([C:18]4([CH2:22][C:23]#[N:24])[CH2:21][N:20]([CH2:37][C:38]([F:41])([F:40])[F:39])[CH2:19]4)[CH:17]=3)[N:10]3[CH:25]=[CH:26][N:27]=[C:9]3[CH:8]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 67459438HCID 67459438, compound

Product 1

HCID 67456817HCID 67456817, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(3-(4-(7-cyclopropylimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile trihydrochloride (100 mg; 0.233 mmol) and acetonitrile (2 mL) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (108 mg; 0.466 mmol) and TEA (118 mg; 1.17 mmol). The mixture was stirred in a sealed vial for 15 hours. Water (40 mL) was added and the mixture was extracted into methylene chloride (3×30 mL). The combined extracts were dried (sodium sulfate and magnesium sulfate), filtered and concentrated under reduced pressure. The material was purified by chromatography on silica gel, eluting with methylene chloride/6% ammonium hydroxide in methanol (98:2-96:4 gradient) to give the desired product as a white foam (56 mg). MS (apci) m/z=402.1 (M+H).

Workup

  1. extractionthe mixture was extracted into methylene chloride (3×30 mL)
  2. dry with materialThe combined extracts were dried (sodium sulfate and magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe material was purified by chromatography on silica gel
  6. washeluting with methylene chloride/6% ammonium hydroxide in methanol (98:2-96:4 gradient)

Sources & evidence

ORD record
ord-541b8b5123ca41ec926c5d4dda425895
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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