Methyl 3-(chlorosulfonyl)-4-methoxybenzoate → 3-[2-(Benzo[b]thiophene-2-sulfonylamino)phenylsulfamoyl]-4-methoxybenzoic acid methyl ester

HRID 730207노트

반응식

HRID 730207 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1)(=[O:11])=[O:10].Cl[S:22]([C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[C:28]([O:30][CH3:31])=[O:29])(=[O:24])=[O:23]>C(Cl)Cl.N1C=CC=CC=1>[CH3:31][O:30][C:28](=[O:29])[C:27]1[CH:32]=[CH:33][C:34]([O:35][CH3:36])=[C:25]([S:22](=[O:23])(=[O:24])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][S:9]([C:12]2[S:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH:13]=2)(=[O:11])=[O:10])[CH:26]=1

참가 물질

5

반응물 2

HCID 2794613Methyl 3-(chlorosulfonyl)-4-methoxybenzoateHCID 86240018Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amide

생성물 1

HCID 116851903-[2-(Benzo[b]thiophene-2-sulfonylamino)phenylsulfamoyl]-4-methoxybenzoic acid methyl ester수율 65.7%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)-amide (1 mmol) in DCM (2 mL) and pyridine (2 mL), methyl 3-(chlorosulfonyl)-4-methoxybenzoate (1.1 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (10 mL). The organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL) and brine (10 mL). The organic phase was dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to obtain 350 mg of 3-[2-(benzo[b]thiophene-2-sulfonylamino)phenylsulfamoyl]-4-methoxybenzoic acid methyl ester. Tr 1.10 min, MS: 533.7 (M+1)+. 1H NMR (CDCl3, 400 MHz): δ 3.84 (s, 3H), 4.18 (s, 3H), 7.0-7.2 (m, 5H), 7.4-7.6 (m, 3H), 7.66 (s, 1H), 7.80 (d, 1H), 7.83 (d, 1H), 8.22 (dd, 1H), 8.34 (d, 1H) ppm.

후처리

  1. washThe organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL) and brine (10 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by flash column chromatography
  6. washeluting with DCM/EtOAc

출처 및 근거

ORD 기록
ord-489cef9e3c8142ecbab82c1b31076875
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582673B2

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