Hydrochloric Acid → HCID 87113395, compound

A mixture of Example 52D (1.59 g, 4.94 mmol) and oxalic acid (0.71 g, 7.9 mmol) in THF (16 mL)/water (8 mL) was stirred at ambient temperature for 2 hr. Additional oxalic acid (0.71 g, 7.9 mmol) and THF (16 mL) were added and the reaction mixture was stirred for 2 additional hr. HCl (4 N in dioxane, 5 mL) was then added and the reaction mixture was stirred 16 hr at ambient temperature, and then quenched by addition of saturated aq Na2CO3 solution (10 mL). The mixture was partitioned between Et2O and H2O, and the separated aqueous phase was extracted with Et2O. The combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified on silica gel (Analogix® Intelliflash 280™; SF25-120 g column; 100% hexane 7 min, then 0% to 20% EtOAc/hexanes eluant, 23 min) which yielded 1.13 g (83%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.98 (s, 1H), 8.27-8.21 (m, 2H), 7.97 (dd, J=9.0, 0.6, 2H). MS (DCI+) m/z 293 (M+NH4).

1. stirringthe reaction mixture was stirred 16 hr at ambient temperature
2. customquenched by addition of saturated aq Na2CO3 solution (10 mL)
3. customThe mixture was partitioned between Et2O and H2O
4. extractionthe separated aqueous phase was extracted with Et2O
5. extractionThe combined organic extract
6. washwas washed with brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude product was purified on silica gel (Analogix® Intelliflash 280™

ORD record

ord-4973294e264d42158d46abbf8cb45e10

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998993B2