Dimethylformamide → HCID 89657583, compound

To a solution of Example 252g (0.10 g, 0.21 mmol) in anhydrous dichloromethane (5 mL) was added oxalyl chloride (0.037 mL, 0.42 mmol) and dimethylformamide (0.816 μl, 10.5 μmol) The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated. The residue was redissolved in dichloromethane (5 mL) and treated with ammonium hydroxide (2 mL, 92 mmol) and the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was partitioned between water (15 mL) and ethyl acetate (25 mL). The aqueous layer was extracted with additional ethyl acetate (2×15 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was triturated with ethyl acetate and the resulting solid was filtered, washed with dichloromethane and dried under vacuo to provide the title compound (48 mg, 47% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.33 (s, 1H), 7.98 (s, 1H), 7.98-7.88 (m, 1H), 7.82 (s, 1H), 7.56-7.40 (m, 4H), 7.19 (m, 1H), 7.00 (d, J=8.8 Hz, 1H), 6.87 (s, 1H), 3.59 (s, 3H), 3.27 (s, 3H). MS (ESI+) m/z 474.1 (M+H)+

1. concentrationThe reaction mixture was concentrated
2. dissolutionThe residue was redissolved in dichloromethane (5 mL)
3. stirringthe reaction mixture was stirred at ambient temperature for 16 hours
4. customThe reaction mixture was partitioned between water (15 mL) and ethyl acetate (25 mL)
5. extractionThe aqueous layer was extracted with additional ethyl acetate (2×15 mL)
6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was triturated with ethyl acetate
10. filtrationthe resulting solid was filtered
11. washwashed with dichloromethane
12. customdried under vacuo

ORD record

ord-42551a27aa8341cd96eaf20668ed9661

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296741B2