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

HRID 597925노트

반응식

HRID 597925 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8eab951586b64fa0ad8f72a616d778c2
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897595B2

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