Trifluoroacetic acid → 2-Fluoro-4-(2-(piperidin-4-yl)-benzo[d]oxazol-5-yl)-benzamide 2,2,2-trifluoroacetate
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)=[N:15][C:14]=3[CH:31]=2)=[CH:6][C:5]=1[F:32])(=[O:3])[NH2:2].[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>C(Cl)Cl>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[F:32][C:5]1[CH:6]=[C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[CH:31]=2)[CH:8]=[CH:9][C:4]=1[C:1]([NH2:2])=[O:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Tert-butyl 4-[5-(4-carbamoyl-3-fluorophenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylate (190 mg, 0.32 mmol) dissolved in DCM (40 ml) and added trifluoroacetic acid (1.5 ml). This mixture stirred at rt for 3 h. After completion of the reaction, DCM removed on rotavapour and residue was co-distilled with ether to obtain 2-fluoro-4-(2-(piperidin-4-yl)-benzo[d]oxazol-5-yl)-benzamide 2,2,2-trifluoroacetate (190 mg). 2-Fluoro-4-(2-(piperidin-4-yl)-benzo[d]oxazol-5-yl)-benzamide 2,2,2-trifluoroacetate (190 mg, 0.42 mmol) was dissolved in DMF (7 ml) and added isobutyric acid (47 mg, 0.46 mmol), EDC.HCl (200 mg, 1.04 mmol), HOBt (70 mg, 0.5 mmol) and TEA (0.7 ml, 3.3 mmol). After completion of the reaction, water added to the reaction mixture to obtain solid. Solid was filtered and washed with ether to obtain the titled compound (120 mg) as a brown solid. M.P.: 193-196° C. MS (m/z): 410.2 [M+H]+.
Workup
- customremoved on rotavapour and residue
Sources & evidence
- ORD record
- ord-b845b9e95dc04a0da8fe2ddf894529cc
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181214B2
Reaction notes
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