Pyridine → HCID 10684544, compound

To a mixture of 3-(4-t-butylbenzoylamino)thiophene-2-carboxylic acid (8.09 g, 27 mmol) and methylene chloride (135 mL) was added oxalyl chloride (11.8 mL, 135 mmol). The mixture was heated until bubbling began. The reaction was stirred for 2 h without heating. The reaction was concentrated and the residue was dissolved in methylene chloride (135 mL). To this solution was added pyridine (2.2 mL, 27 mmol) and stirred at room temperature for 1 h. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with water (4 times) and brine, MgSO4 dried and concentrated. The residue was chromatographed (10% ethyl acetate/hexanes) to afford the title compound as a solid (7.44 g, 96%); NMR(CDCl3) d 1.37(s, 9H), 7.35(d, J=5.1 Hz, 1H), 7.52(d, J=8.4 Hz, 2H), 7.91(d, J=5.1 Hz, 1H), 8.22(d, J=8.4 Hz, 2H); MS(FD): 285.

1. temperatureThe mixture was heated
2. customuntil bubbling
3. temperaturewithout heating
4. concentrationThe reaction was concentrated
5. dissolutionthe residue was dissolved in methylene chloride (135 mL)
6. stirringstirred at room temperature for 1 h
7. concentrationThe reaction mixture was concentrated
8. custompartitioned between ethyl acetate and water
9. washThe organic layer was washed with water (4 times) and brine, MgSO4
10. customdried
11. concentrationconcentrated
12. customThe residue was chromatographed (10% ethyl acetate/hexanes)

ORD record

ord-ac104b0cb6834b2f8ac76e51947212c5

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677369B2