Hydrochloric Acid → HCID 69222961, compound

Temperature

0 °C

A solution of 1-(4-(2,3-dihydrobenzo[b][1,4]dioxin-6-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)-3,3,3-trifluoropropan-1-one (0.069 g, 0.17 mmol) in THF (5 mL) was cooled to 0° C. under nitrogen. Lithium aluminum hydride was added (0.85 ml of a 1.0M solution in THF, 0.85 mmol) and the mixture was stirred at 0° C. for one h. The mixture was allowed to gradually warm to r.t. with overnight stirring and then cooled again to 0° C. Water (1 mL) was added dropwise. After five min, 10N NaOH (1 mL) was added and the mixture was allowed to warm to r.t. Water (3 mL) was added. The mixture was then extracted with ethyl acetate (2×15 mL). The combined organic extracts were washed with water and brine and dried over sodium sulfate. The solvent was concentrated to leave an oil which was purified by silica gel chromatography (ethyl acetate/hexane gradient). The colorless oil so obtained (0.020 g) was dissolved in diethyl ether and treated with 1.0 M HCl in diethyl ether (0.05 mL) to produce a solid which was triturated with diethyl ether and dried to yield the product (17 mg).

1. temperatureto gradually warm to r.t. with overnight
2. stirringstirring
3. temperaturecooled again to 0° C
4. waitAfter five min
5. temperatureto warm to r.t
6. extractionThe mixture was then extracted with ethyl acetate (2×15 mL)
7. washThe combined organic extracts were washed with water and brine
8. dry with materialdried over sodium sulfate
9. concentrationThe solvent was concentrated
10. customto leave an oil which
11. customwas purified by silica gel chromatography (ethyl acetate/hexane gradient)
12. customThe colorless oil so obtained (0.020 g)
13. customto produce a solid which
14. customwas triturated with diethyl ether
15. customdried

ORD record

ord-34177d242edb46228f256ba9689720c8

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07414131B2