Trifluoroacetic acid → HCID 71253604, compound

Temperature

105 °C

In a high-pressure vessel was placed 1-methyl-5-(methylamino)-4-(3-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)pyrrolidin-2-one 259 (70.0 mg, 0.17 mmol) and trifluoroacetic acid (5 mL). The vessel was sealed and the reaction mixture was stirred at 105° C. for 20 h. The reaction mixture was cooled to RT, and triethylsilane (0.50 mL) was added. The vessel was resealed, and the reaction mixture was stirred at 75° C. After 2 h, more triethylsilane (0.5 mL) was added at RT, and the reaction mixture was stirred in a sealed vessel at 95° C. for 17 h. Volatile solvent was evaporated in vacuo. The resultant crude oil was dissolved in DMF (2 mL). Black insoluble material was filtered and rinsed well with methanol (2×2 mL). The combined filtrates were evaporated in vacuo and the crude product was purified by reverse phase HPLC to give 263 as a white solid (12.7 mg, 25.2%). 1H NMR (400 MHz, DMSO) δ 13.37 (broad s, 1H), 9.08 (s, 1H), 8.04 (d, J=7.4 Hz, 2H), 7.98 (s, 1H), 7.54 (t, J=7.6 Hz, 2H), 7.44 (d, J=7.4 Hz, 1H), 3.98-3.85 (m, 1H), 3.75 (t, J=9.0 Hz, 1H), 3.53 (dd, J=9.3, 7.2 Hz, 1H), 2.78 (s, 3H), 2.66 (dd, J=8.8, 2.9 Hz, 2H). LC/MS: m/z 293.1 [M+1]

1. customIn a high-pressure vessel was placed
2. customThe vessel was sealed
3. temperatureThe reaction mixture was cooled to RT
4. stirringthe reaction mixture was stirred at 75° C
5. waitAfter 2 h
6. stirringthe reaction mixture was stirred in a sealed vessel at 95° C. for 17 h
7. customVolatile solvent was evaporated in vacuo
8. dissolutionThe resultant crude oil was dissolved in DMF (2 mL)
9. filtrationBlack insoluble material was filtered
10. washrinsed well with methanol (2×2 mL)
11. customThe combined filtrates were evaporated in vacuo
12. customthe crude product was purified by reverse phase HPLC

ORD record

ord-b079266ed16041cdb8ce9fa7cac2f958

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260425B2