Methanol → 3-(Benzyloxy)-N,N-diethyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide

HRID 1016685ノート

反応式

HRID 1016685 の反応式
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH2:13]([O:20][C:21]1[C:26](=[O:27])[CH:25]=[C:24]([CH3:28])O[C:22]=1[C:29]([OH:31])=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33].CN.CO>CN(C=O)C>[CH2:13]([O:20][C:21]1[C:26](=[O:27])[CH:25]=[C:24]([CH3:28])[N:3]([CH3:1])[C:22]=1[C:29]([N:34]([CH2:35][CH3:36])[CH2:32][CH3:33])=[O:31])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

7

反応物 5

HCID 887MethanolHCID 6329MethylamineHCID 8021DiethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 98564973-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

生成物 1

HCID 120106513-(Benzyloxy)-N,N-diethyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide収率 68.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

1,1′-carbonyldiimidazole (1.87 g, 111.53 mmol) was added to a solution of the 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (2.0 g, 7.69 mmol) in DMF (15 ml) at room temperature. The resulting solution was heated at 40° C. for 3 hrs. A clear yellow solution was observed. Diethylamine (1.08 ml, 9.2 mmol) was added. The reaction mixture was stirred at 40 to 45° C. for 2 hrs. The reaction was cooled to room temperature at which time a solution of methylamine in methanol (11 ml of 2M solution in methanol, 15.4 mmol) was added. The solution was stirred at 65 to 70° C. for 15 hrs under pressure. The solvent was removed under reduced pressure and dichloromethane was added (70 ml). The solution was washed with water and dried over magnesium sulfate (1 g). Solvent evaporation gave light yellow oil as a crude product. The column was eluted with 10% to 25% methanol in ethyl acetate to give the titled compound (1.74 g, yield 67%). H-NMR (CDCl3) σ: 1.09 (t, J=7.11 Hz, 3H, Me), 1.16 (t, J=7.04 Hz 3H, Me), 2.34 (s, 3H, Me), 3.13-3.30 (m, 2H, CH2), 3.47 (s, 3H, NMe), 3.50-3.60 (m, 2H, CH2), 4.91(d, J=10.76 Hz, 1H, CH2), 5.52(d, J=10.74 Hz, 1H, CH2), 6.41 (s, 1H, CH), 7.10-7.33 (m, 5H, Ph), Mass spect. 329 (M+1).

後処理

  1. additionwas added
  2. stirringThe solution was stirred at 65 to 70° C. for 15 hrs under pressure
  3. customThe solvent was removed under reduced pressure and dichloromethane
  4. additionwas added (70 ml)
  5. washThe solution was washed with water
  6. dry with materialdried over magnesium sulfate (1 g)
  7. customSolvent evaporation
  8. customgave light yellow oil as a crude product
  9. washThe column was eluted with 10% to 25% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-cc3a3fab4b50426aab49c12bddea1912
出典データセット
uspto-grants-2002_11
特許番号
US06476229B1

反応ノート

読み込み中…