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

HRID 1438491노트

반응식

HRID 1438491 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-46c92657e7af450486f0ce4d607e7077
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622583B2

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