Chlorosuccinimide → HCID 68231181, compound

HRID 1853022Notes

Reaction equation

HRID 1853022 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([C:18]4([CH2:27][C:28]#[N:29])[CH2:21][N:20]([CH2:22][C:23]([F:26])([F:25])[F:24])[CH2:19]4)[CH:17]=3)[N:10]3[CH:30]=[CH:31][N:32]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1.C([O-])(O)=O.[Na+].[Cl:38]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:38][C:30]1[N:10]2[C:11]([C:13]3[CH:14]=[N:15][N:16]([C:18]4([CH2:27][C:28]#[N:29])[CH2:21][N:20]([CH2:22][C:23]([F:24])([F:26])[F:25])[CH2:19]4)[CH:17]=3)=[N:12][C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)=[CH:8][C:9]2=[N:32][CH:31]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 674576832-(3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoro ethyl)azetidin-3-yl)acetonitrile

Product 1

HCID 68231181HCID 68231181, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoro ethyl)azetidin-3-yl)acetonitrile (Example 71, 100 mg, 0.227 mmol) in DCM (1.5 mL) was added saturated NaHCO3 (1.0 mL) followed by N-chlorosuccinimide (46.3 mg, 0.340 mmol) in one portion. The biphasic mixture was vigorously stirred at ambient temperature for 17 hours and was diluted with DCM (2 mL). The solution was washed with H2O, dried over Na2SO4 and eluted through a silica gel plug (EtOAc elution). The solution was concentrated, the residual glass was dissolved in minimal DCM and hexane was added to afford a granular suspension. The suspension was concentrated and the residual solid was washed with warm 25% EtOAc/hexanes and dried in vacuum to afford the title compound (22 mg, 20% yield) as an ivory white powder. MS (apci) m/z=476.1 (M+H).

Workup

  1. washThe solution was washed with H2O
  2. dry with materialdried over Na2SO4
  3. washeluted through a silica gel plug (EtOAc elution)
  4. concentrationThe solution was concentrated
  5. dissolutionthe residual glass was dissolved in minimal DCM
  6. additionhexane was added
  7. customto afford a granular suspension
  8. concentrationThe suspension was concentrated
  9. washthe residual solid was washed
  10. temperaturewith warm 25% EtOAc/hexanes
  11. customdried in vacuum

Sources & evidence

ORD record
ord-284e27d6c6dd443db576dffd3bde1226
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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