Water → 4-[7-Methoxy-8-methyl-2-(4-trifluoromethyl-thiazol-2-yl)-quinolin-4-yloxy]-piperidine-2-carboxylic acid methyl ester

HRID 880736Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]([O:11][C:12]2[C:21]3[C:16](=[C:17]([CH3:24])[C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[N:15]=[C:14]([C:25]3[S:26][CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:29]=3)[CH:13]=2)[CH2:8][CH2:7][N:6]1C(OCC1C=CC=CC=1)=O)=[O:4].O>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]([O:11][C:12]2[C:21]3[C:16](=[C:17]([CH3:24])[C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[N:15]=[C:14]([C:25]3[S:26][CH:27]=[C:28]([C:30]([F:31])([F:33])[F:32])[N:29]=3)[CH:13]=2)[CH2:8][CH2:7][NH:6]1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of compound 13 (1.08 g) in trifluoroacetic acid (17 mL) was stirred at 60° C. for 5 hrs. The solution was then cooled down at 0° C., water was added, and the mixture was extracted with EtOAc. Organics were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (DCM/MeOH) to yield compound 14 as a white powder in 97% yield. MS (ESI, EI+) m/z=482 (MH+).

Workup

temperatureThe solution was then cooled down at 0° C.
extractionthe mixture was extracted with EtOAc
washOrganics were washed with saturated NaHCO3
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude material was purified by chromatography on silica gel (DCM/MeOH)

Sources & evidence

ORD record: ord-148150503bcf4abb816e1d6b3fc14e12
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993595B2

Reaction notes

Loading…