2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 86685322, compound

HRID 1853030Notes

Reaction equation

HRID 1853030 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([C:14]3([CH2:18][C:19]#[N:20])[CH2:17][NH:16][CH2:15]3)[CH:13]=2)[N:6]2[CH:21]=[CH:22][N:23]=[C:5]2[CH:4]=1.CCN(C(C)C)C(C)C.FC(F)(F)S(O[CH2:39][C:40]([F:43])([F:42])[F:41])(=O)=O>CN(C=O)C>[Cl:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([C:14]3([CH2:18][C:19]#[N:20])[CH2:17][N:16]([CH2:39][C:40]([F:43])([F:42])[F:41])[CH2:15]3)[CH:13]=2)[N:6]2[CH:21]=[CH:22][N:23]=[C:5]2[CH:4]=1

Participants

5

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 81531DiisopropylethylamineHCID 86685319HCID 86685319, compound

Product 1

HCID 86685322HCID 86685322, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 1.5 mL of DMF were combined 2-(3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (0.059 g, 0.14 mmol), DIEA (0.15 mL, 0.84 mmol), and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.049 g, 0.21 mmol) and allowed to proceed at ambient temperature with stirring. After 2 hours the DMF was removed under reduced pressure with heating and the crude was purified by means of silica gel chromatography eluting with 1:1 EtOAc/hexanes containing 0.25% NH4OH to afford 2-(3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoro ethyl)azetidin-3-yl)acetonitrile (0.034 g, 0.086 mmol, 62% yield). MS (apci) m/z=396.1 (M+H).

Workup

  1. customto proceed at ambient temperature
  2. customAfter 2 hours the DMF was removed under reduced pressure
  3. temperaturewith heating
  4. customthe crude was purified by means of silica gel chromatography
  5. washeluting with 1:1 EtOAc/hexanes containing 0.25% NH4OH

Sources & evidence

ORD record
ord-e459b432680d47389cb7516df3477729
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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