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

HRID 1801036Notes

Reaction equation

HRID 1801036 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:15]2[C:24]([CH3:26])([CH3:25])[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:27]([OH:29])=O)[CH:21]=3)[NH:16]2)[CH:6]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=1)#[N:2].Cl.CN(C)CCCN=C=NCC.[CH3:42][S:43]([NH2:46])(=[O:45])=[O:44]>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:15]2[C:24]([CH3:26])([CH3:25])[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:27]([NH:46][S:43]([CH3:42])(=[O:45])=[O:44])=[O:29])[CH:21]=3)[NH:16]2)[CH:6]=[C:7]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67441006HCID 67441006, compound

Product 1

HCID 53491764N-[2-(3-cyano-5-morpholin-4-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamideYield 30%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-(3-cyano-5-morpholin-4-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (60 mg, 0.15 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (44 mg, 0.23 mmol), 4-dimethylaminopyridine (28 mg, 0.23 mmol), methane sulfonamide (43 mg, 0.45 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 N-[2-(3-cyano-5-morpholin-4-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (21 mg, 30%) as a light yellow solid: LC/MS m/e calcd for C24H28N4O4S (M+H)+: 469.6, observed: 469.2.

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-7d7070f1c40542c6ba2cfa7cb6eba05f
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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