HCID 67281830, compound → HCID 67281889, compound

HRID 1187458Notes

Reaction equation

HRID 1187458 reaction equation
C([O:8][C:9]1[C:10](=[O:22])[CH:11]=[C:12]([CH:19]([F:21])[F:20])[N:13]([CH2:15][CH:16]2[CH2:18][CH2:17]2)[CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH:16]1([CH2:15][N:13]2[CH:14]=[C:9]([OH:8])[C:10](=[O:22])[CH:11]=[C:12]2[CH:19]([F:21])[F:20])[CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 67281830HCID 67281830, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67281889HCID 67281889, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-benzyloxy-1-cyclopropylmethyl-2-difluoromethyl-1H-pyridin-4-one (3.0 g, 9.82 mmol) and 10% Pd/C (300 mg) in methanol (90 mL) was subjected to hydrogenation in a Parr apparatus under a 15 psi hydrogen pressure for 27 min. Work-up as described above for the cyclopropyl derivative, afforded the title product (1.76 g, 83% yield) after vacuum oven drying. HPLC purity (peak area percent) of the title compound is 99.5% at λ=288 nm using HPLC Method 1 as described above.

Sources & evidence

ORD record
ord-fb8b069d3dcd48939d9abf7171881afa
Source dataset
uspto-grants-2014_03
Patent number
US08673943B2

Reaction notes

Loading…