Triethylamine → HCID 86724384, compound

To a mixture of 2-[4-chloro-3-methyl-5-(trifluoromethyl)pyrazol-1-yl]acetic acid (0.150 g, 0.62 mmol) in CH2Cl2 (2 mL) was added oxalyl chloride (0.15 mL, 1.75 mmol) and DMF (1 drop). The mixture was stirred for 30 min at room temperature and was then concentrated in vacuo. The solid obtained was transferred to another flask containing 1-(4-fluorophenyl)pyrazol-4-amine (0.080 g, 0.45 mmol) and NEt3 (0.25 mL, 1.8 mmol) in CH2Cl2 (3 mL). The mixture was stirred for 30 min at room temperature, treated with water (50 mL), and extracted with ethyl acetate (50 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (SiO2, 0-50% EtOAc/hexanes gradient elution) to give the title compound as a white solid (0.084 g, 47%). 1H NMR (400 MHz CDCl3) δ 8.40 (s, 1H), 7.71 (s, 1H), 7.69 (m, 2H), 7.19 (dd, J=8.4, 8.4 Hz, 2H), 5.07 (s, 2H), 2.34 (s, 3H); MS: (ES) m/z calculated for C16H12ClF4N5O [M+H]+ 402.0, found 402.0.

1. concentrationwas then concentrated in vacuo
2. customThe solid obtained
3. customwas transferred to another flask
4. stirringThe mixture was stirred for 30 min at room temperature
5. extractionextracted with ethyl acetate (50 mL)
6. customThe organic layer was separated
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated in vacuo
9. custompurified by flash chromatography (SiO2, 0-50% EtOAc/hexanes gradient elution)

ORD record

ord-08575301ca5845d0afb24fe4fc874763

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169248B2