Methanol → 3-ethyl-2-methoxy-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine

HRID 597925ノート

反応式

HRID 597925 の反応式
[CH2:1]([C:3]1[C:20]([O:21][CH3:22])=[N:19][C:6]2[CH2:7][CH2:8][N:9](C(=O)C(F)(F)F)[CH2:10][CH:11]([CH3:12])[C:5]=2[CH:4]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].CO>O>[CH2:1]([C:3]1[C:20]([O:21][CH3:22])=[N:19][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH:11]([CH3:12])[C:5]=2[CH:4]=1)[CH3:2]

参加物

5

反応物 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 236542823-ethyl-2-methoxy-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine

生成物 1

HCID 236539033-ethyl-2-methoxy-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine収率 40.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2-methoxy-5-methyl-7-(trifluoroacetyl)-3-vinyl-6,7,8,9-tetrahydro -5H-pyrido[2,3-d]azepine (52 mg, 166 μmol), 5% Pd/C (20 mg), and MeOH (20 ml) was stirred under H2 (1 atm) for 15 h. Filtration and concentration of the filtrate in vacuo yielded 36.0 mg (69%) of 3-ethyl-2-methoxy-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. MS (ESI) m/z 317.3. A mixture of 3-ethyl-2-methoxy-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine (36.0 mg, 114 μmol), K2CO3 (100 mg), MeOH (5 ml) and H2O (1 ml) was heated to reflux for 10 min. The reaction mixture was concentrated in vacuo and the resulting residue was purified by column chromatography to yield 10.2 mg (40%) of 3-ethyl-2-methoxy-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. 1H-NMR (MeOH-d4) δ 7.30 (s, 1H), 3.89 (s, 3H), 3.17 (m, 5H), 3.06 (m, 1H), 2.87 (m, 1H), 2.57 (m, 2H), 1.31 (d, 3H), 1.15 (t, 3H) ppm.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 10 min
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe resulting residue was purified by column chromatography

出典と根拠

ORDレコード
ord-8eab951586b64fa0ad8f72a616d778c2
出典データセット
uspto-grants-2011_03
特許番号
US07897595B2

反応ノート

読み込み中…