Water → HCID 67508116, compound

HRID 1431727Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:14]2[CH:15]=[N:16][C:17](F)=[CH:18][CH:19]=2)[C:3]=1[CH3:21].[CH3:22][N:23]([CH3:29])[CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([N:26]3[CH2:27][CH2:28][CH:24]([N:23]([CH3:29])[CH3:22])[CH2:25]3)=[N:16][CH:15]=2)[C:3]=1[CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 4-chloro-5,7-difluoro-2-(6-fluoropyridin-3-yl)-3-methylquinoline (0.1 g, 0.32 mmol) in DMF (3.0 mL) was added 3-(dimethylamino)-pyrrolidine (0.041 mL, 0.32 mmol) followed by potassium carbonate (0.090 g, 0.65 mmol). The reaction was stirred at 100° C. and stirring continued for 19 h. After which, the reaction mixture was cooled to rt and water was added. The crude mixture was extracted with EtOAc and dried over magnesium sulfate and concd in vacuo. The crude material was purified on silica gel, eluting with 0-30% EtOAc in hexanes to provide 1-(5-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2-yl)-N,N-dimethylpyrrolidin-3-amine as a white solid. Mass Spectrum (ESI) m/e=403.1 (M+1).

Workup

stirringstirring
temperatureAfter which, the reaction mixture was cooled to rt
extractionThe crude mixture was extracted with EtOAc
dry with materialdried over magnesium sulfate and concd in vacuo
customThe crude material was purified on silica gel
washeluting with 0-30% EtOAc in hexanes

Sources & evidence

ORD record: ord-bc514955d2b84cecb62e195c78ac55c9
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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