Methanesulfonamide → N-[2-(3-dimethylamino-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide

HRID 2045263Notes

Reaction equation

HRID 2045263 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:4]=[C:5]([CH:10]2[C:19]([CH3:21])([CH3:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:22]([OH:24])=O)[CH:16]=3)[NH:11]2)[CH:6]=[C:7]([F:9])[CH:8]=1.Cl.CN(C)CCCN=C=NCC.[CH3:38][S:39]([NH2:42])(=[O:41])=[O:40]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:25][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([CH:10]2[C:19]([CH3:21])([CH3:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:22]([NH:42][S:39]([CH3:38])(=[O:41])=[O:40])=[O:24])[CH:16]=3)[NH:11]2)[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 674407372-(3-Dimethylamino-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

Product 1

HCID 53492646N-[2-(3-dimethylamino-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamideYield 42%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(3-dimethylamino-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (10 mg, 0.03 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.4 mg, 0.044 mmol), 4-dimethylaminopyridine (5.4 mg, 0.044 mmol), methane sulfonamide (8.3 mg, 0.09 mmol) in dichloromethane (3 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-dimethylamino-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (5 mg, 42%) as a light yellow solid: LC/MS m/e calcd for C21H26FN3O3S (M+H)+: 420.5, observed: 420.1.

Workup

  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)

Sources & evidence

ORD record
ord-d657d5b0663248908094b55e9212bd5a
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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