Ethyl Acetate → HCID 178522278, 화합물

HRID 1279392

반응식

HRID 1279392 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 178522278HCID 178522278, 화합물수율 63.8%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2e03889c17d84a12abaa655de8a9befb
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448274B2

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