Pyridine → 2-(4-(5-(5-Phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethanol
Reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=O)[C:8]=2[CH2:15][CH2:16][CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.N1C(F)=NC(F)=NC=1F.O/[N:34]=[C:35](\[NH2:45])/[C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][OH:44])=[CH:38][CH:37]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.C(OCC)(=O)C>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:14][N:45]=[C:35]([C:36]4[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][OH:44])=[CH:38][CH:37]=4)[N:34]=3)[C:8]=2[CH2:15][CH2:16][CH3:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
To a mixture of 5-phenyl-4-propylisoxazole-3-carboxylic acid (385 mg, 1.665 mmol) and pyridine (0.135 mL, 1.665 mmol) in DCM (5 mL) was added cyanuric fluoride (0.141 mL, 1.665 mmol). The reaction mixture was stirred for 1 hour. The reaction mixture was diluted with dichloromethane and washed with 1M HCl. The organic layer was dried MgSO4, filtered and concentrated. This crude residue was dissolved in acetonitrile (5.00 mL). (Z)—N′-hydroxy-4-(2-hydroxyethyl)benzimidamide (300 mg, 1.665 mmol) and DIEA (0.582 mL, 3.33 mmol) were added. The reaction mixture was heated at 75° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with sat NaCl. The organic layer was dried MgSO4, filtered, and concentrated to yield 800 mg of 2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethanol. MS (m+1)=376. HPLC Peak RT=2.09 minutes. (Analytical Method B).
Workup
- washwashed with 1M HCl
- filtrationfiltered
- concentrationconcentrated
- dissolutionThis crude residue was dissolved in acetonitrile (5.00 mL)
- washwashed
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7403b3e843c84998a2be617ce93ed932
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399451B2
Reaction notes
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