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

HRID 597925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597925
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 236539033-ethyl-2-methoxy-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepineAusbeute 40,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8eab951586b64fa0ad8f72a616d778c2
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897595B2

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