Trifluoroacetic acid → HCID 59924650, compound

HRID 2300885Notes

Reaction equation

HRID 2300885 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([O:25][CH2:26][CH:27]5[CH2:31][CH2:30][CH2:29][N:28]5C(OCC5C=CC=CC=5)=O)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>CO.[OH-].[OH-].[Pd+2]>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([O:25][CH2:26][CH:27]5[CH2:31][CH2:30][CH2:29][NH:28]5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59924884HCID 59924884, compound

Product 1

HCID 59924650HCID 59924650, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

2-[(S)-1-Phenylethylamino]-4-[5-((N-benzyloxycarbonyl-pyrrolidin-2-yl)methoxy)benzimidazol-1-yl]pyrimidine (11 mg) was dissolved in methanol (1.0 mL) and catalytic Pd(OH)2 and trifluoroacetic acid were added and the resulting suspension was stirred under hydrogen atmosphere for 15 hours. Filtration and evaporation of solvent gave N-[(1S)-1-phenylethyl]-4-[5-(2-pyrrolidinylmethoxy)-1H-benzimidazol-1-yl]-2-pyrimidinamine (7.0 mg). Mass spectrum (ESI) 415.5 (M+1).

Workup

  1. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-05d5be6a5cc64075a1bd0ed7b18a7c9d
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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