Benzenesulfonyl chloride, 3,4-dichloro- → 3,4-dichloro-N-[5-chloro-2-(2-chloro-benzoyl)-pyridin-3-yl]-benzenesulfonamide

HRID 1898055ノート

反応式

HRID 1898055 の反応式
[NH2:1][C:2]1[C:3]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:18][C:19]1[CH:20]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1[Cl:25]>N1C=CC=CC=1>[Cl:18][C:19]1[CH:20]=[C:21]([S:26]([NH:1][C:2]2[C:3]([C:9](=[O:10])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=2)(=[O:27])=[O:28])[CH:22]=[CH:23][C:24]=1[Cl:25]

参加物

4

反応物 2

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 57942272(3-Amino-5-chloro-pyridin-2-yl)-(2-chloro-phenyl)-methanone

生成物 1

HCID 116053303,4-dichloro-N-[5-chloro-2-(2-chloro-benzoyl)-pyridin-3-yl]-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

A mixture of (3-amino-5-chloro-pyridin-2-yl)-(2-chloro-phenyl)-methanone (26.8 mg, 0.10 mmol) and 3,4-dichloro-benzenesulfonyl chloride (24.5 mg, 0.10 mmol) in anhydrous pyridine (1 mL) were stirred overnight at 60° C. Reaction mixture was concentrated and the residue was treated with 1 M NaOH (5 mL) and THF (5 mL) to hydrolyze bis-sulfonamide. The resultant solution was neutralized to pH 6 and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The was purified by preparative HPLC (20→90% gradient of MeCN-water) and pure product fractions were lyophilized to provide 3,4-dichloro-N-[5-chloro-2-(2-chloro-benzoyl)-pyridin-3-yl]-benzenesulfonamide as a solid. MS m/z: 498.0 (M+Na).

後処理

  1. customReaction mixture
  2. concentrationwas concentrated
  3. additionthe residue was treated with 1 M NaOH (5 mL) and THF (5 mL)
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe was purified by preparative HPLC (20→90% gradient of MeCN-water) and pure product fractions

出典と根拠

ORDレコード
ord-00c4e7545fd04a1f9ba5374a4e42dc98
出典データセット
uspto-grants-2013_08
特許番号
US08519135B2

反応ノート

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