Water → HCID 52913378, compound

A stirred solution of 2-{3-[3-(3-aminooxetan-3-yl)phenyl]-5-(4-trifluoromethylphenoxy)-1H-pyrazol-1-yl}-N,N-dimethylacetamide (46 mg, 0.10 mmol) in 1 mL of CH2Cl2 was cooled in an ice bath. Triethylamine (0.021 mL, 0.15 mmol) was added, followed by trifluoroethylsulfonyl chloride (0.013 mL, 0.12 mmol), and the mixture was stirred for 30 min. Water was added and the mixture was extracted with CH2Cl2. The combined organic phases were washed with water and brine, then dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. The residue was purified on a C18 reverse phase column using a gradient elution of 20-70% CH3CN:H2O with 0.1% TFA over 20 min at 20 mL/min. Fractions containing pure product were combined and the solvents were removed under reduced pressure to give 2-[5-(4-trifluoromethylphenoxy)-3-(3-{3-[(2,2,2-trifluoroethylsulfonyl)amino]oxetan-3-yl}phenyl)-1H-pyrazol-1-yl]-N,N-dimethylacetamide as a foam. Calcd (M+1)+: 607.1444. Found: 607.1468. 1H NMR (400 MHz, CDCl3) δ 7.75 (m, 2H), 7.64 (d, J=7, 2H), 7.44 (t, J=7, 1H), 7.35 (m, 2H), 7.28 (s, 1H), 6.38 (s, 1H), 6.04 (s, 1H), 5.04 (d, J=7, 2H), 4.98 (d, J=7, 2H), 4.94 (s, 2H), 3.09 (s, 3H), 2.97 (overlapping s and q, 5H).

1. extractionthe mixture was extracted with CH2Cl2
2. washThe combined organic phases were washed with water and brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. customthe solvent was removed under reduced pressure
6. customThe residue was purified on a C18 reverse phase column
7. washa gradient elution of 20-70% CH3CN
8. waitH2O with 0.1% TFA over 20 min at 20 mL/min
9. additionFractions containing pure product
10. customthe solvents were removed under reduced pressure

ORD record

ord-5a9008afed1d4b62b35c860f67778408

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871796B2