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Methanesulfonamide → 4-[(5-Chloro-6-fluoropyridin-3-yl)oxy]-2,5-difluoro-N-(methylsulfonyl)benzamide

HRID 2048055
ノート
印刷プレビュー

反応式

HRID 2048055 の反応式
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C1CCN2C(=NCCC2)CC1.[Cl:17][C:18]1[CH:19]=[C:20]([O:25][C:26]2[C:41]([F:42])=[CH:40][C:29]([C:30](OC3C=CC(C)=CC=3)=[O:31])=[C:28]([F:43])[CH:27]=2)[CH:21]=[N:22][C:23]=1[F:24]>CC#N.CCOC(C)=O>[Cl:17][C:18]1[CH:19]=[C:20]([O:25][C:26]2[C:41]([F:42])=[CH:40][C:29]([C:30]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:31])=[C:28]([F:43])[CH:27]=2)[CH:21]=[N:22][C:23]=1[F:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58042398p-Tolyl 4-(5-chloro-6-fluoropyridin-3-yloxy)-2,5-difluorobenzoate

生成物 1

HCID 580423644-[(5-Chloro-6-fluoropyridin-3-yl)oxy]-2,5-difluoro-N-(methylsulfonyl)benzamide収率 36.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
45 °C

実験手順

Methanesulfonamide (52.0 mg, 0.547 mmol) was suspended in MeCN (3 mL) in a sealed vial. 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine (0.085 mL, 0.57 mmol) was added followed by 4-methylphenyl 4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2,5-difluorobenzoate (Preparation 67, 215.0 mg, 0.546 mmol). The mixture was heated at 45° C. for 2 hours. The reaction mixture was diluted in EtOAc (15 mL), then washed with 10% aqueous citric acid solution (2×15 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting solid was partitioned between DCM (10 mL) and water (10 mL). The organic layer was further washed water (2×10 mL) and concentrated in vacuo to yield the title compound as a white solid (75 mg). EtOAc (15 mL) was added to the combined aqueous. The organic layer was then washed with water (3×10 mL), dried over sodium sulfate, filtered and concentrated in vacuo to yield a second batch of the title compound as a white solid (75.0 mg, 35%):

後処理

  1. washwashed with 10% aqueous citric acid solution (2×15 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid was partitioned between DCM (10 mL) and water (10 mL)
  6. washThe organic layer was further washed water (2×10 mL)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8998601744e04895b9f43ef675d76ee3
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592629B2

反応ノート

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