Triethylamine → N-(1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide

Temperature

-10 °C

To a stirred solution of benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1 g, 3.5 mmol) in tetrahydrofuran was added triethylamine (1 mL, 7 mmol). The mixture was cooled to −10° C. and cyclopropanecarbonyl chloride (0.53 mL, 5.3 mmol) was added drop wise. The reaction mixture was stirred at room temperature for 1 hour, followed by concentration under vacuum to remove tetrahydrofuran. The residue was dissolved in ethyl acetate and organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to give the crude mixture of benzyl 4-[bis(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate and benzyl 4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate. The mixture was treated with a saturated potassium carbonate solution in methanol and stirred at room temperature followed by removal of methanol under vacuum at the same temperature. The residue was treated drop wise with saturated aqueous sodium bicarbonate solution and the precipitated solid was filtered, washed with water and dried to yield N-(1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide (0.5 g, 69%) as a pale yellow solid.

1. concentrationfollowed by concentration under vacuum
2. customto remove tetrahydrofuran
3. dissolutionThe residue was dissolved in ethyl acetate
4. washorganic layer was washed with water
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated
7. customto give the crude
8. stirringstirred at room temperature
9. customfollowed by removal of methanol under vacuum at the same temperature
10. additionThe residue was treated drop wise with saturated aqueous sodium bicarbonate solution
11. filtrationthe precipitated solid was filtered
12. washwashed with water
13. customdried

ORD record

ord-36697401e8724a19969b2743ffcd8539

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980911B2