Carbamate → 1-(3-(7-Chloroimidazo[1,2-a]pyridin-3-yl)phenyl)-3-(2,2,2-trifluoroethyl)urea

HRID 2274239

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=3)[NH2:14])=[CH:9][N:10]=[C:4]2[CH:3]=1.C(Cl)(=O)OC1C=CC([N+]([O-])=O)=CC=1.CCN(C(C)C)C(C)C.[C:40](=[O:43])([O-])[NH2:41].[F:44][C:45]([F:49])([F:48])[CH2:46]N>C1COCC1.CCOC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([NH:14][C:40]([NH:41][CH2:46][C:45]([F:49])([F:48])[F:44])=[O:43])[CH:15]=[CH:16][CH:17]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-(7-chloroimidazo[1,2-a]pyridin-3-yl)aniline (0.15 mmol) in THF (1.5 mL) was added 4-nitrophenyl carbonochloridate (30 mg, 0.15 mmol) and DIEA (0.036 mL, 0.225 mmol). The mixture was heated at 60° C. for 6 h. To the crude carbamate was added DIEA (0.036 mL, 0.225 mmol) and 2,2,2-trifluoroethan-1-amine (0.014 mL, 0.18 mmol) and the solution was heated at 60° C. overnight. The reaction mixture was diluted with EtOAc and water. The separated organic layer was dried with sodium sulfate, filtered and concentrated. The crude mixture was purified by flash chromatography (0-6% MeOH/DCM) to give the title compound (38 mg, 69% yield). MS (ES+) C16H12ClF3N4O requires: 368. Found: 369 [M+H]+.

Workup

temperaturethe solution was heated at 60° C. overnight
dry with materialThe separated organic layer was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude mixture was purified by flash chromatography (0-6% MeOH/DCM)

Sources & evidence

ORD record: ord-27a86f1aeb604a81903a6c5a62be2a87
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126951B2

Linked notes

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