Methanesulfonamide → N-[2-(4'-tert-butyl-5-fluoro-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide

HRID 2045260노트

반응식

HRID 2045260 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([CH:18]3[C:27]([CH3:29])([CH3:28])[CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:30](O)=[O:31])[CH:24]=4)[NH:19]3)[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:33][S:34]([NH2:37])(=[O:36])=[O:35]>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([CH:18]3[C:27]([CH3:29])([CH3:28])[CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:30]([NH:37][S:34]([CH3:33])(=[O:36])=[O:35])=[O:31])[CH:24]=4)[NH:19]3)[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 72879MethanesulfonamideHCID 674427452-(4'-Tert-butyl-5-fluoro-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

생성물 1

HCID 53492645N-[2-(4'-tert-butyl-5-fluoro-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide수율 30.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-(4′-tert-butyl-5-fluoro-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (30 mg, 0.07 mmol), 1-3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (20 mg, 0.10 mmol), 4-dimethylaminopyridine (12.2 mg, 0.10 mmol), methane sulfonamide (20 mg, 0.21 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-(4′-tert-butyl-5-fluoro-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (11 mg, 30%) as a light yellow solid: LC/MS m/e calcd for C29H33FN2O3S (M+H)+: 509.66, observed: 509.2.

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-3b666c49216a44a3a446c5c3810b9629
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586747B2

반응 노트

불러오는 중…