Trifluoroacetic acid → HCID 57920202, compound

HRID 2098382Notes

Reaction equation

HRID 2098382 reaction equation
[CH3:1][N:2]([CH3:39])[C:3](=[O:38])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([O:30]CC3C=CC=CC=3)[CH2:19][CH2:18][N:17]([C:20]3[C:21]4[C:28]([CH3:29])=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1.FC(F)(F)C(O)=O>CO.[OH-].[OH-].[Pd+2]>[CH3:39][N:2]([CH3:1])[C:3](=[O:38])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([OH:30])[CH2:19][CH2:18][N:17]([C:20]3[C:21]4[C:28]([CH3:29])=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57920196HCID 57920196, compound

Product 1

HCID 57920202HCID 57920202, compoundYield 14.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Crude 3-(4-(benzyloxy)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate from example 24, step F (85% pure, approximately 80 mg) was taken up in methanol (2 mL), and a catalytic amount of Pearlman's catalyst was added. The system was hydrogenated at 60 psi for 24 hours, after which a small amount of product was observed. Trifluoroacetic acid (0.1 mL) was added, and the hydrogenation was continued at 60 psi H2 for 3 days, after which the reaction was approximately one third of the way completed. The reaction was filtered, and the product was isolated by prep HPLC (30×100 mm C18 column, 10-100% acetonitrile:water (10 mM ammonium acetate), 15 min, 45 mL/min) to afford the title compound (9.6 mg) as a white solid.

Workup

  1. waitthe hydrogenation was continued at 60 psi H2 for 3 days
  2. filtrationThe reaction was filtered
  3. customthe product was isolated by prep HPLC (30×100 mm C18 column, 10-100% acetonitrile:water (10 mM ammonium acetate), 15 min, 45 mL/min)

Sources & evidence

ORD record
ord-6f364bdb664a420ea8071e33177579a8
Source dataset
uspto-grants-2013_05
Patent number
US08450332B2

Reaction notes

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