Potassium Carbonate → N-cyclopropyl-4-methyl-3-({4-[(3-methylpyridin-2-yl)methoxy]benzoyl}amino)benzamide

HRID 403031

反応式

HRID 403031 の反応式
[CH3:1][C:2]1[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH:14]1([NH:17][C:18](=[O:36])[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=3)[CH:20]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C(#N)C>[CH:14]1([NH:17][C:18](=[O:36])[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([NH:26][C:27](=[O:35])[C:28]3[CH:29]=[CH:30][C:31]([O:9][CH2:8][C:3]4[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=4)=[CH:32][CH:33]=3)[CH:20]=2)[CH2:16][CH2:15]1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 1514369(3-Methylpyridin-2-yl)methanolHCID 66631169N-cyclopropyl-3-[(4-hydroxybenzoyl)amino]-4-methylbenzamide

生成物 1

HCID 11165932N-cyclopropyl-4-methyl-3-({4-[(3-methylpyridin-2-yl)methoxy]benzoyl}amino)benzamide収率 102.2%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

To (3-methylpyridine-2-yl)methanol (157 mg, 1.272 mmol) in DCM (5 mL) was added thionyl chloride (200 μl) and the mixture stirred and heated at reflux for 4 h. The mixture was evaporated to dryness. To the residue was added N-cyclopropyl-3-[(4-hydroxybenzoyl)amino]-4-methylbenzamide (197 mg, 0.636 mmol) and potassium carbonate (176 mg, 1.27 mmol) in acetonitrile (5 mL) and the resulting mixture heated at 80° C. for 16 h. The reaction mixture was cooled and partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic phase was concentrated under reduced pressure. Precipitation with DCM in diethyl ether gave the title compound as a solid (270 mg); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.68 (m, 2H), 2.26 (s, 3H), 2.40 (s, 3H), 2.86 (m, 1H), 5.30 (s, 2H), 7.17 (d, 2H), 7.33 (m, 2H), 7.65 (m, 2H), 7.82 (s, 1H), 7.97 (d, 2H), 8.39 (m, 2H), 9.81 (s, 1H); Mass Spectrum: M+H+ 416.

後処理

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. customThe mixture was evaporated to dryness
  4. temperatureThe reaction mixture was cooled
  5. custompartitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  6. concentrationThe organic phase was concentrated under reduced pressure
  7. customPrecipitation with DCM in diethyl ether

出典と根拠

ORDレコード
ord-5edb858c26bf4de9bbd8fb6bd245c791
出典データセット
uspto-grants-2014_06
特許番号
US08742124B2

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