Methylamine → 3-(benzyloxy)-N-cyclobutyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide

HRID 420476Notes

Reaction equation

HRID 420476 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])O[C:10]=1[C:17]([NH:19][CH:20]1[CH2:23][CH2:22][CH2:21]1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][NH2:25]>CO>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[N:25]([CH3:24])[C:10]=1[C:17]([NH:19][CH:20]1[CH2:23][CH2:22][CH2:21]1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 866117983-(benzyloxy)-N-cyclobutyl-6-methyl-4-oxo-4H-pyran-2-carboxamide

Product 1

HCID 666589483-(benzyloxy)-N-cyclobutyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamideYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
72.5 °C

Procedure

To a solution of the compound from example 4 (2.616 g, 8.35 mmol, 1.0 equiv) in methanol (10 ml) was quickly added methylamine (2M in methanol, 20 ml, 40 mmol, 4.79 equiv). The sealed tube was stirred overnight at 70-75° C. The resulting brown solution was evaporated to dryness and purified by chromatography (EtOAc, then 1:4 MeOH/EtOAc) provided the titled compound (1.70 g, 62.24%) as a white solid. M.p. 221.3-222.4° C.; 1H-NMR (DMSO-d6, 400 MHz) δ 1.65-1.69 (m, 2H, cyclobutyl H), 1.90-1.95 (m, 2H, cyclobutyl H), 2.14-2.21 (m, 2H, cyclobutyl H), 2.31 (s, 3H, CH3), 3.42 (s, 3H, NCH3), 4.34-4.30 (m, 1H, CH), 5.05 (s, 2H, OCH2Ph), 6.22 (s, 1H, CH), 7.39-7.30 (m, 5H, ArH), 9.08-9.06 (d, 1H, J=7.08 Hz, NH); MS (m/z) 327 (M++1), 230, 166, 91.

Workup

  1. customThe resulting brown solution was evaporated to dryness
  2. custompurified by chromatography (EtOAc

Sources & evidence

ORD record
ord-a6d5069a688244e0a49bae04eb6d4990
Source dataset
uspto-grants-2012_01
Patent number
US08097624B2

Reaction notes

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