Ethyl Acetate → HCID 178522278、化合物

HRID 1279392

反応式

HRID 1279392 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 178522278HCID 178522278、化合物収率 63.8%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2e03889c17d84a12abaa655de8a9befb
出典データセット
uspto-grants-2002_09
特許番号
US06448274B2

関連ノート

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