Benzenesulfonyl chloride → 3,3-Dimethyl-2-(4-(phenylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 2045541노트

반응식

HRID 2045541 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][CH:3]=1.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[CH3:19][C:17]1([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=2)[NH:9][CH:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])=[CH:7][CH:6]=1

참가 물질

4

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 674414332-(4-Aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

생성물 1

HCID 584761473,3-Dimethyl-2-(4-(phenylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid수율 65%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (100 mg, 0.34 mmol) in pyridine (5 mL) was added benzenesulfonyl chloride (0.05 mL, 0.38 mmol) via syringe with ice cooling. Upon completion of the addition, the resultant mixture was allowed to warm back to room temperature and stir for 24 h. LC-MS showed the reaction was complete. Pyridine was removed in vacuo and the residue was purified by preparative thin layer chromatography to afford 81 mg of 3,3-dimethyl-2-(4-(phenylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Yield: 65%; MS (ESI+APCI) M+1=437.54.

후처리

  1. additionUpon completion of the addition
  2. customPyridine was removed in vacuo
  3. customthe residue was purified by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-927c9e29524c49b99597d47ad59a265c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586747B2

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