4-Fluorobenzohydrazide → HCID 58574138, compound

Temperature

60 °C

A solution of 13-oxo-7,8,9,10,11,13-hexahydro-6H-azocino[2,1-b]quinazoline-3-carboxylic acid (80 mg, 0.28 mmol) in SOCl2 (3 mL) was stirred at reflux for 0.5 h. The reaction mixture was concentrated and diluted with toluene (5 mL). 4-fluorobenzohydrazide (54.4 mg, 0.35 mmol) was added to the solution and heated to 60° C. After stirring for 1.5 h, the toluene was evaporated. Phosphoryl trichloride (3 mL) was added to the residue and heated at 80° C. for 1.5 h. Excess phosphoryl trichloride was removed under reduced pressure and diluted with water (25 mL). The mixture was adjusted to pH around 7 with aqueous Na2CO3 solution. The aqueous mixture was extracted with ethyl acetate (3×20 mL), dried over Na2SO4. After filtration, the filtrate was concentrated and purified by column chromatography to give the desired product (7 mg). MS (ESI): 391 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.43-8.39 (m, 2H), 8.23-8.16 (m, 3H), 7.29 (s, 1H), 7.24 (s, 1H), 4.38 (s, 2H), 3.11-3.07 (t, J=6.1 Hz, 2H), 2.05-1.93 (m, 4H), 1.65 (m, 2H), 1.49 (broad, 2H).

1. temperatureat reflux for 0.5 h
2. concentrationThe reaction mixture was concentrated
3. additiondiluted with toluene (5 mL)
4. customthe toluene was evaporated
5. additionPhosphoryl trichloride (3 mL) was added to the residue
6. temperatureheated at 80° C. for 1.5 h
7. customExcess phosphoryl trichloride was removed under reduced pressure
8. additiondiluted with water (25 mL)
9. extractionThe aqueous mixture was extracted with ethyl acetate (3×20 mL)
10. dry with materialdried over Na2SO4
11. filtrationAfter filtration
12. concentrationthe filtrate was concentrated
13. custompurified by column chromatography

ORD record

ord-f4db082360694b7bbae11fd178164a0e

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772301B2