1-(1-Cyclopentyl-2-cyclopropylethyl)-1H-pyrazol-4-yl-7H-pyrrolo[2,3-d]pyrimidine trifluoroacetate salt → HCID 66597459, compound

HRID 1817653Notes

Reaction equation

HRID 1817653 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]1([CH:13]([N:18]2[CH:22]=[C:21]([C:23]3[N:24]=[CH:25][C:26]4[CH:31]=[CH:30][NH:29][C:27]=4[N:28]=3)[CH:20]=[N:19]2)[CH2:14][CH:15]2[CH2:17]C2)[CH2:12][CH2:11][CH2:10][CH2:9]1.[H][H]>CO.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]1([CH:13]([N:18]2[CH:22]=[C:21]([C:23]3[C:31]4[CH:26]=[CH:25][NH:24][C:30]=4[N:29]=[CH:27][N:28]=3)[CH:20]=[N:19]2)[CH2:14][CH2:15][CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 866130141-(1-Cyclopentyl-2-cyclopropylethyl)-1H-pyrazol-4-yl-7H-pyrrolo[2,3-d]pyrimidine trifluoroacetate saltHCID 178418361HCID 178418361, compound

Product 1

HCID 66597459HCID 66597459, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[1-(1-Cyclopentylbut-3-yn-1-yl)-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]pyrimidine trifluoro-acetate salt (prepared in Example 729) (20 mg, 0.048 mmol) was dissolved in methanol (2 mL) and a catalytic amount of 5% Pd—C was added. The mixture was stirred under 1 atmosphere of hydrogen via an affixed balloon. After 2 hours, 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 the product (14 mg, 69%).

Workup

  1. filtrationthe mixture was filtered
  2. custompurified via preparative-HPLC/MS (C18
  3. washeluting with a gradient of H2O and ACN containing 0.1% TFA)

Sources & evidence

ORD record
ord-2e147711e8104932be6b7beb8a73acf3
Source dataset
uspto-grants-2009_10
Patent number
US07598257B2

Reaction notes

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