HCID 178425160, compound → HCID 178425161, compound

HRID 1501184Notes

Reaction equation

HRID 1501184 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[CH:16]=[CH:15][C:14]([CH:17]([N:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]3=[O:25])[CH3:18])=[CH:13][CH:12]=2)=[C:6]([CH3:27])[CH:5]=[C:4]([CH3:28])[N:3]=1>CO.[Pd]>[OH:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[CH:12]=[CH:13][C:14]([CH:17]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]3=[O:25])[CH3:18])=[CH:15][CH:16]=2)=[C:6]([CH3:27])[CH:5]=[C:4]([CH3:28])[N:3]=1

Participants

4

Reactant 1

HCID 178425160HCID 178425160, compound

Product 1

HCID 178425161HCID 178425161, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-(2-oxopyridin-1(2H)-yl)ethyl)benzamide (30 mg, 0.08 mmol) in methanol was added palladium on carbon (30 mg). The mixture was stirred at room temperature for 12 hours under hydrogen atmosphere. Then the mixture was filtered and the filtrate was concentrated to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-(2-oxopiperidin-1-yl)ethyl)benzamide (21 mg, 67%). LRMS (M+H) m/z: calcd 381.19. found 381. HPLC purity (214 nm): 95%. 1H NMR (300 MHz, CD3OD): δ 7.78 (d, J=8.1 Hz, 2H), 7.36 (d, J=8.1 Hz, 2H), 6.10 (s, 1H), 6.00 (q, J=6.9 Hz, 1H), 4.49 (s, 2H), 3.23-3.19 (m, 1H), 2.83-2.79 (m, 1H), 2.46-2.42 (m, 2H), 2.36 (s, 3H), 2.24 (s, 3H), 1.81-1.63 (m, 4H), 1.54 (d, J=6.9 Hz, 3H).

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-61fb962e968a4e5e94ce5cab1fa9ff09
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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