Cyclopropanesulfonamide → Cyclopropanesulfonic acid [2-(3-cyclohexyl-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide

HRID 1801039Notes

Reaction equation

HRID 1801039 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]([CH:14]3[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:26](O)=[O:27])[CH:20]=4)[NH:15]3)[CH:10]=[C:11]([F:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:29]1([S:32]([NH2:35])(=[O:34])=[O:33])[CH2:31][CH2:30]1>CN(C)C1C=CN=CC=1.ClCCl>[CH:1]1([C:7]2[CH:8]=[C:9]([CH:14]3[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:26]([NH:35][S:32]([CH:29]5[CH2:31][CH2:30]5)(=[O:34])=[O:33])=[O:27])[CH:20]=4)[NH:15]3)[CH:10]=[C:11]([F:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 15765418CyclopropanesulfonamideHCID 674411792-(3-Cyclohexyl-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

Product 1

HCID 53491831Cyclopropanesulfonic acid [2-(3-cyclohexyl-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amideYield 20.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-(3-cyclohexyl-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (60 mg, 0.16 mmol), 1-3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (45 mg, 0.24 mmol), 4-dimethylaminopyridine (29 mg, 0.24 mmol), cyclopropane sulfonamide (58 mg, 0.48 mmol) in dichloromethane (10 mL) was heated at 65° C. 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 cyclopropanesulfonic acid [2-(3-cyclohexyl-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (16 mg, 20%) as a light yellow solid: LC/MS m/e calcd for C27H33FN2O3S (M+H)+: 485.6, observed: 485.3.

Workup

  1. customRemoval of the solvent
  2. customafforded an oil residue
  3. 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)

Sources & evidence

ORD record
ord-e6470b5204054022bc4a12d48c2aae6c
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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