Trifluoroacetic acid → 4-Chloro-5,7-difluoro-3-methyl-2-(piperazin-1-yl)quinoline 2,2,2-trifluoroacetate

HRID 1431645Notes

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]([N:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[C:3]=1[CH3:27].[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>ClCCl>[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[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]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:3]=1[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

The tert-butyl 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate (370 mg, 0.93 mmol) was dissolved in dichloromethane (3.0 mL) and cooled to 0° C. The trifluoroacetic acid (0.50 mL, 6.5 mmol) was added and the mixture was stirred for 2 h while warming to rt. The mixture was then cond and triturated with EtOAc. The slurry was filtered to give 4-chloro-5,7-difluoro-3-methyl-2-(piperazin-1-yl)quinoline 2,2,2-trifluoroacetate. Mass Spectrum (ESI) m/e=298.1 (M+1).

Workup

temperaturewhile warming to rt
customcond and triturated with EtOAc
filtrationThe slurry was filtered

Sources & evidence

ORD record: ord-5b0424d490af4a17afc9b565a1b6a4eb
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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