Methanesulfonamide → N-(2-{3-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonyl)-methanesulfonamide

HRID 1801077노트

반응식

HRID 1801077 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[C:16]([CH:20]4[C:29]([CH3:31])([CH3:30])[CH2:28][C:27]5[C:22](=[CH:23][CH:24]=[C:25]([C:32](O)=[O:33])[CH:26]=5)[NH:21]4)[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:35][S:36]([NH2:39])(=[O:38])=[O:37]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[C:16]([CH:20]4[C:29]([CH3:30])([CH3:31])[CH2:28][C:27]5[C:22](=[CH:23][CH:24]=[C:25]([C:32]([NH:39][S:36]([CH3:35])(=[O:38])=[O:37])=[O:33])[CH:26]=5)[NH:21]4)[CH:17]=[CH:18][CH:19]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 72879MethanesulfonamideHCID 584762472-{3-[4-(4-Chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

생성물 1

HCID 53491975N-(2-{3-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonyl)-methanesulfonamide수율 26%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-{3-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (100 mg, 0.21 mmol), 1-3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (60.5 mg, 0.32 mmol), 4-dimethylaminopyridine (39 mg, 0.32 mmol), methane sulfonamide (60 mg, 0.63 mmol) in dichloromethane (10 mL) was refluxed for 12 hours. Removal of the solvent afforded an oil residue. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded N-(2-{3-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonyl)-methanesulfonamide (30 mg, 26%) as a light yellow solid: LC/MS m/e calcd for C29H33ClN4O3S M+: 553.13, observed: 553.2.

후처리

  1. temperaturewas refluxed for 12 hours
  2. customRemoval of the solvent
  3. customafforded an oil residue
  4. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water)

출처 및 근거

ORD 기록
ord-b0ddb8bf684b4ea68e6aca5034a0cd35
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344137B2

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