Diisopropylethylamine → {4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2'-methylbiphenyl-2-YL}methanol
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([C:8](=[N:10][OH:11])[NH2:9])[CH:7]=1.[OH:14][CH2:15][C:16]1[CH:21]=[C:20]([C:22](O)=O)[CH:19]=[CH:18][C:17]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31].Cl.C(N=C=NCCCN(C)C)C.CCN(C(C)C)C(C)C>C1COCC1.C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([C:8]2[N:9]=[C:22]([C:20]3[CH:19]=[CH:18][C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:31])=[C:16]([CH2:15][OH:14])[CH:21]=3)[O:11][N:10]=2)[CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
Intermediate 23 (276 mg; 1.5 mmol; 1 eq.), Intermediate 41 (436 mg; 1.8 mmol; 1.2 eq.) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (345 mg; 1.8 mmol; 1.2 eq.) were dissolved in THF (6 mL) and acetonitrile (6 mL) and the reaction mixture was stirred at room temperature for 2 hours. DIEA (0.61 mL; 3.6 mmol; 2.4 eq.) was added and the mixture was heated in the microwave at 150° C. for 30 min. The reaction mixture was then filtered through a SPE-NH2 column (2 g) and through a SPE-SCX column (2 g) and rinsed with ACN. The filtrate was evaporated and the residue washed with ACN to afford the title compound as a white solid.
Workup
- filtrationThe reaction mixture was then filtered through a SPE-NH2 column (2 g)
- washthrough a SPE-SCX column (2 g) and rinsed with ACN
- customThe filtrate was evaporated
- washthe residue washed with ACN
Sources & evidence
- ORD record
- ord-fee5f96c193a4464ac5a4ced30751e8c
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889668B2
Reaction notes
Loading…