Potassium Carbonate → 2-[3-(6-Methanesulfonylaminocarbonyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-2-methyl-propionic acid ethyl ester

HRID 1800918Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[O:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:27][O:28][C:29](=[O:34])[C:30](Br)([CH3:32])[CH3:31].[C:35](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:27]([O:28][C:29](=[O:34])[C:30]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[O:21])[CH:14]=3)[NH:9]2)[CH:3]=1)([CH3:32])[CH3:31])[CH3:35]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of N-[2-(3-Amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (0.37 g, 1 mmol), 2-bromo-2-methyl-propionic acid methyl ester (0.39 mL, 3 mmol) and potassium carbonate (690 mg, 5 mmol) in N,N-dimethylformamide (6 mL) was stirred at 25° C. for 96 h. Then the reaction mixture was extracted with ethyl acetate (2×100 mL), washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-[3-(6-methanesulfonylaminocarbonyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-2-methyl-propionic acid ethyl ester (47 mg, 10%) as a brown oil which was used for next step without further purification: LC/MS m/e calcd for C24H31N3O5S (M+H)+: 474.60, observed: 474.1.

Workup

extractionThen the reaction mixture was extracted with ethyl acetate (2×100 mL)
washwashed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bb804b30eae94cf98b1139cac4aa140a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344137B2

Reaction notes

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