Triethylamine → HCID 71061549, compound

Temperature

-10 °C

Benzyl 4-amino-3-chloro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (350 mg, 1.16 mmol) was stirred in tetrahydrofuran and triethylamine (0.32 mL, 2.3 mmol) was added. The mixture was cooled to −10° C. and cyclopropanecarbonyl chloride (0.2 mL, 1.73 mmol) was added drop wise. The reaction mixture was stirred at room temperature for about 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]-3-chlorol H-pyrrolo[3,2-c]pyridine-1-carboxylate and benzyl 4[(cyclopropylcarbonyl)amino]-3-chloro1H-pyrrolo[3,2-c]pyridine-1-carboxylate. The mixture was treated with saturated potassium carbonate solution in methanol (1 mL) and stirred at room temperature. After completion, methanol was removed under vacuum at room temperature. The residue was treated drop wise with saturated aq. sodium bicarbonate solution and the precipitated solid was filtered, washed with water and dried to obtain N-(3-chloro-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide (176 mg, 69%) as a white 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. customAfter completion, methanol was removed under vacuum at room temperature
10. additionThe residue was treated drop wise with saturated aq. sodium bicarbonate solution
11. filtrationthe precipitated solid was filtered
12. washwashed with water
13. customdried

ORD record

ord-0d80998eed6f4f74bc582a33e5b5d349

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980911B2