Triethylamine → 2-chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

Triethylamine (0.76 mL, 5.47 mmol) then ethyl chloroformate (0.52 mL, 5.47 mmol) were added to N-[1-(carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 2; 2.0 g, 4.97 mmol) in anhydrous THF (40 mL) at 0° C. followed by stirring for 1 h. LiBH4 (2.0 M in THF, 3.1 mL, 6.21 mmol) was added slowly and the mixture stirred for a further 30 min. The reaction was carefully quenched with 1M HCl (200 mL) and EtOAc (400 mL) and the organic layer was further washed with sat. aqueous NaHCO3 (100 mL), brine (100 mL), dried (MgSO4), filtered and evaporated. The residue was triturated with refluxing Et2O (30 mL) and after cooling the solid was filtered and dried to afford the title compound (1.70 g, 88%) as a white solid.

1. stirringthe mixture stirred for a further 30 min
2. customThe reaction was carefully quenched with 1M HCl (200 mL) and EtOAc (400 mL)
3. washthe organic layer was further washed with sat. aqueous NaHCO3 (100 mL), brine (100 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. customThe residue was triturated with refluxing Et2O (30 mL)
8. temperatureafter cooling the solid
9. filtrationwas filtered
10. customdried

ORD record

ord-faac4678271e4f5581e5883b95b6af82

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129249B2