HCID 67281830, compound → HCID 67281889, compound

HRID 912992Notes

Reaction equation

HRID 912992 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. 1H NMR (400 MHz, DMSO-D6) δ (ppm): 7.65 (s, 1H), 7.19 (t, J=52.6 Hz, 1H, CF2H), 6.48 (s, 1H), 3.88 (d, J=7.1 Hz, 2H, N—CH2), 1.19 (m, 1H), 0.45-0.57 (m, 4H); MS-ESI (m/z): 216.1 [M+1]+, 55.2 (100%); Anal. Calcd. for C10H11F2NO2: C, 55.81; H, 5.15; N, 6.51%. Found: C, 56.20; H, 5.44; N, 6.40%.

Sources & evidence

ORD record
ord-159c176bc0cf4892a8e901cc0176e2d6
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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