Ethyl Acetate → HCID 178522278, Verbindung

HRID 1279392

Reaktionsgleichung

Reaktionsgleichung von HRID 1279392
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[NH:8][C:9](=[O:25])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:19])[F:18])=[C:12]([O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)[CH:11]=1.O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:37].[Mg+2].C(OCC)(=O)C>C(Cl)Cl.CO>[Cl:26][C:6]1[CH:5]=[N+:4]([O-:37])[CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9](=[O:25])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:18])[F:19])=[C:12]([O:20][CH2:21][CH:22]2[CH2:23][CH2:24]2)[CH:11]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 449193RoflumilastHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)2×

Produkt 1

HCID 178522278HCID 178522278, VerbindungAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

A mixture of N-(3,5-Dichloropyridin-4-yl)-4-difluoromethoxy-3-cyclopropylmethoxybenzamide (3.0 g, 7.4 mmol) and magnesium monoperoxyphthalate hexahydrate (“MMPP”) (7.36 g, 14.9 mmol) in CH2Cl2/MeOH (10 mL) was stirred under reflux for 48 h. An additional amount of magnesium monoperoxyphthalate hexahydrate (7.4 g, 15 mmol) was added and the reaction mixture was stirred under reflux for an additional 24 h. Ethyl acetate was then added and the organic phase was washed by 25% aqueous NH4OAc, water and brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica (EtOAc) to yield N-(3.5-Dichloro-1-oxido-pyridin-4-yl)-4-difluoromethoxy-3-cyclopropylmethoxybenzamide (Compound I) as a white solid (1.98 g, 63%). 1H NMR (500 MHz, acetone-d6): δ 0.40 (m, 2H), 0.60 (m, 2H), 1.30 (m, 1H), 4.0 (d, 2H), 7.05 (t, 1H), 7.35 (d, 1H), 7.7 (m, 1H), 7.75 (s, 1H), 8.40 (s, 2H), 9.6 (bs, 1H).

Aufarbeitung

  1. temperatureunder reflux for 48 h
  2. stirringthe reaction mixture was stirred
  3. temperatureunder reflux for an additional 24 h
  4. washthe organic phase was washed by 25% aqueous NH4OAc, water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-2e03889c17d84a12abaa655de8a9befb
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06448274B2

Verknüpfte Notizen

Wird geladen…