Triethylamine → 4-Fluoro-N-((1R,3S)-3-hydroxycyclohexyl)-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxamide
Reaction equation
[F:1][C:2]1[C:3]([C:17]([OH:19])=O)=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[NH2:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][C@H:23]([OH:27])[CH2:22]1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[F:1][C:2]1[C:3]([C:17]([NH:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][C@H:23]([OH:27])[CH2:22]2)=[O:19])=[N:4][O:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:12]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-fluoro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylic acid (19 mg, 0.07 mmol), (1S,3R)-3-aminocyclohexanol (9.3 mg, 0.081 mmol), 1-hydroxybenzotriazole hydrate (9.0 mg, 0.07 mmol), and triethylamine (10 μL, 0.07 mmol) in tetrahydrofuran (1 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (15 mg. 0.081 mmol). After stirring overnight, the volatiles were removed in vacuo and the compound was purified by silica gel chromatography eluting with 5% methanol in dichloromethane to afford the title compound: (12.1 mg, 0.03 mmol). MS (ESI) m/z (M+H+): 373.2.
Workup
- customthe volatiles were removed in vacuo
- customthe compound was purified by silica gel chromatography
- washeluting with 5% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-4ecf6e5eb09741ea90b01d60b4de2ba4
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211927B2
Reaction notes
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