Dimethylformamide → HCID 69932817, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl {3-[3-(5-(4-trifluoromethylphenoxy)-1H-pyrazol-3-yl)phenyl]oxetan-3-yl}carbamate from Example 130, Step 7 (120 mg, 0.25 mmol), 4-chloromethyloxazole (119 mg, 1.0 mmol), and K2CO3 (155 mg, 1.1 mmol) in 0.6 mL of DMF were combined in a sealed tube and the stirred mixture was heated to 100° C. for 18 h. The mixture was cooled to ambient temperature and diluted with CH2Cl2. The mixture was washed with water and brine, then dried over Na2SO4, filtered, and the solvents were reduced under reduced pressure to give an oil. The residue was purified on a C18 column using a gradient elution of 20-100% CH3CN:H2O with 0.1% TFA. Fractions containing the first eluting peak were combined and the solvents were removed under reduced pressure to give compound A, tert-butyl (3-{3-[5-(4-trifluoromethylphenoxy)-1-(1,3-oxazol-4-ylmethyl)-1H-pyrazol-3-yl]phenyl}oxetan-3-yl)carbamate, as a glass. Calcd 557.5. found: 557.8. 1H NMR (400 MHz, CDCl3) δ 7.88 (br s, 1H), 7.65 (m, 3H), 7.50 (d, J=7, 1H), 7.41 (t, J=7, 1H), 7.25 (d, J=7, 2H), 7.08 (s, 1H), 6.06 (s, 1H), 5.45 (s, 2H), 5.01 (br s, 2H), 4.89 (br d, 2H), 1.20 (br s, 9H). Fractions containing the second eluting peak were combined and the solvents were removed under reduced pressure to give compound B, tert-butyl (3-{3-[3-(4-trifluoromethylphenoxy)-1-(1,3-oxazol-4-ylmethyl)-1H-pyrazol-5-yl]phenyl}oxetan-3-yl)carbamate, as a glass. Calcd (M+1)+: 557.5. found: 557.9. 1H NMR (400 MHz, CDCl3) δ 7.45-7.775 (m, 6H), 7.25 (d, J=7, 2H), 7.16 (s, 1H), 5.98 (s, 1H), 5.85 (s, 2H), 4.99 (br 5, 2H), 4.87 (br d, 2H), 1.20 (br s, 9H).

Provenance & Evidence