HCID 66898270, compound → (S)-2-((5-hydroxy-1-methyl-4-oxo-1,4-dihydropyridin-2-yl)methylamino)-N-methylpropanamide

HRID 1519056Notes

Reaction equation

HRID 1519056 reaction equation
C([O:8][C:9]1[C:10](=[O:24])[CH:11]=[C:12]([CH2:16][NH:17][C@@H:18]([CH3:23])[C:19]([NH:21][CH3:22])=[O:20])[N:13]([CH3:15])[CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][C:9]1[C:10](=[O:24])[CH:11]=[C:12]([CH2:16][NH:17][C@@H:18]([CH3:23])[C:19]([NH:21][CH3:22])=[O:20])[N:13]([CH3:15])[CH:14]=1

Participants

5

Reactant 2

HCID 66898270HCID 66898270, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70805245(S)-2-((5-hydroxy-1-methyl-4-oxo-1,4-dihydropyridin-2-yl)methylamino)-N-methylpropanamideYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-2-((5-(benzyloxy)-1-methyl-4-oxo-1,4-dihydropyridin-2-yl)methylamino)-N-methylpropanamide (7.04 g, 21.4 mmol) and 10% Pd/C (0.90 g) in MeOH (70 mL) was subjected to hydrogenation in a Parr apparatus at 50 psi of hydrogen pressure for 2 h. The reaction mixture was filtered over celite and the filtrate was concentrated in vacuo. The resulting solid was dried in a vacuum oven at 44° C. for overnight. Thus, (S)-2-((5-hydroxy-1-methyl-4-oxo-1,4-dihydropyridin-2-yl)methylamino)-N-methylpropanamide was obtained as an orange solid (4.90 g) in 96% yield. 1H NMR (CD3COOD) δ (ppm): 7.77 (s, 1H), 7.03 (s, 1H), 4.30-4.34 (m, 3H, OCH2+CHCH3), 3.98 (s, 3H), 2.80 (s, 3H), 1.56 (d, J=6.3 Hz, 3H, CHCH3); MS m/z 262 [M+Na]+, 240 (100%) [M+1]+, 138, 110.

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting solid was dried in a vacuum oven at 44° C. for overnight

Sources & evidence

ORD record
ord-6ada1f6d5d914aa8908f86d3ea02e9ac
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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