Diisopropylethylamine → HCID 90011400, compound

Step-5: 5-(1-(5-Bromopyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2(3H)-one: To a stirred and (0° C.) cooled solution of step-4 intermediate (4.0 g, 11.43 mmol) and DIPEA (3.99 mL, 22.85 mmol) in DCM (50 mL) was added a solution of triphosgene (1.35 g, 4.57 mmol) in DCM (20 mL) over a period of 10 min. Reaction mixture was warmed to room temperature and stirred overnight. The reaction was cooled to 0° C. and quenched with ice water (5 mL). Water (25 mL) was added to the above mixture followed by DCM (100 mL). The layers were separated and the aqueous layer was extracted with DCM (2×100 mL). The combined organic layers were washed with brine (50 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 3.0 g (70%) of the title compound as pink semisolid. 1HNMR (400 MHz, DMSO-d6) δ 12.95 (s, 1H, D2O exchangeable), 8.71 (d, J=2.5 Hz, 1H), 8.39 (dd, J=2.5 & 8.5 Hz, 1H), 7.90 (d, T=8.5 Hz, 1H), 7.70 (s, 1H); ESI-MS (m/z) 376, 378 [(MH)+, Br79,81].

1. customReaction mixture
2. temperatureThe reaction was cooled to 0° C.
3. customquenched with ice water (5 mL)
4. additionWater (25 mL) was added to the above mixture
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with DCM (2×100 mL)
7. washThe combined organic layers were washed with brine (50 mL)
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. customThe filtrate was rotary evaporated

ORD record

ord-b44d35e9c9994f46a107a95c4a9ecb54

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409898B2