HCID 66597460, compound → 4-[1-(1-Cyclopentyl-4,4-difluorobutyl)-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]-pyrimidine trifluoroacetate salt

HRID 41011Notes

Reaction equation

HRID 41011 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]1([CH:13]([N:19]2[CH:23]=[C:22]([C:24]3[C:25]4[CH:32]=[CH:31][NH:30][C:26]=4[N:27]=[CH:28][N:29]=3)[CH:21]=[N:20]2)[CH2:14][CH:15]=[C:16]([F:18])[F:17])[CH2:12][CH2:11][CH2:10][CH2:9]1>CO.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]1([CH:13]([N:19]2[CH:23]=[C:22]([C:24]3[C:25]4[CH:32]=[CH:31][NH:30][C:26]=4[N:27]=[CH:28][N:29]=3)[CH:21]=[N:20]2)[CH2:14][CH2:15][CH:16]([F:17])[F:18])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 66597460HCID 66597460, compound

Product 1

HCID 665975734-[1-(1-Cyclopentyl-4,4-difluorobutyl)-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]-pyrimidine trifluoroacetate saltYield 21.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[1-(1-Cyclopentyl-4,4-difluorobut-3-en-1-yl)-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]-pyrimidine trifluoroacetate salt (prepared as in Example 731) (20.0 mg, 0.041 mmol) was dissolved in methanol (3 mL), and a catalytic amount of 5% Pd on C was added. The mixture was stirred at room temperature for 2 hours, under an atmosphere of hydrogen provided by an affixed balloon. The mixture was filtered and purified via preparative-HPLC/MS (C18 eluting with a gradient of H2O and ACN containing 0.1% TFA) to afford product (4 mg, 21%).

Workup

  1. customprovided by an affixed balloon
  2. filtrationThe mixture was filtered
  3. custompurified via preparative-HPLC/MS (C18
  4. washeluting with a gradient of H2O and ACN containing 0.1% TFA)

Sources & evidence

ORD record
ord-0e1501c6d3bf46669ab02a5cc568991f
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Reaction notes

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