Trifluoroacetic acid → HCID 22936265, compound

HRID 387868Notes

Reaction equation

C(OC(=O)[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]2[S:35][CH:36]=[CH:37][N:38]=2)=[O:32])=[C:26]([F:39])[CH:25]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1>>[NH2:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]2[S:35][CH:36]=[CH:37][N:38]=2)=[O:32])=[C:26]([F:39])[CH:25]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7520Thioanisole

HCID 58931466HCID 58931466, compound

Product 1

HCID 22936265HCID 22936265, compoundYield 30.3%

Conditions

Temperature: 60 °C

Procedure

After adding {4-[3-fluoro-4-(3-(thiazol-2-yl)ureido)phenoxy]-7-methoxyquinolin-6-yl}carbamic acid benzyl ester (100 mg) to a mixture of trifluoroacetic acid (3 ml) and thioanisole (0.1 ml), the mixture was heated and stirred at 60° C. for 2 hours. The solvent was distilled off and the residue was subjected to NH silica gel column chromatography for elution with a solvent (ethyl acetate:methanol=10:1) to obtain the title compound (23 mg) as a solid.

Workup

temperaturethe mixture was heated
distillationThe solvent was distilled off
washthe residue was subjected to NH silica gel column chromatography for elution with a solvent (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record: ord-34c3067c478c46c79ec31ab3776eaeee
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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