Dichloromethane → HCID 59242746, compound

Temperature

5 °C

Add (±)-2-amino-4-pyridin-2-ylmethyl-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile hydrochloride (35 g, 108 mmol) to a mixture of dichloromethane (350 mL) and pyridine (70 mL). Stir the mixture under nitrogen and cool to 5° C. Add isopropyl chloroformate (1M solution in toluene, 162 mL, 162 mmol). Remove the ice bath and stir the mixture at 22° C. After 16 h evaporate the solvent. Add the resulting residue to water (350 mL) and stir 2 h. Filter and dry the collected solid under vacuum at 45° C. Add the solid to ethyl acetate (400 mL) and heat the mixture to reflux. Then cool to 22° C. and filter the solid. Add the wet solid to ethyl acetate (200 mL) and heat to reflux for 30 min. Cool the mixture to 22° C. over one hour and then cool to 0-5° C. during 5 min. Filter the mixture and dry the isolated solid under vacuum to constant weight to provide 23 g (62%) of the title compound. MS (m/z): 374 (M+1).

1. customRemove the ice bath
2. stirringstir the mixture at 22° C
3. customAfter 16 h evaporate the solvent
4. additionAdd the resulting residue to water (350 mL)
5. stirringstir 2 h
6. filtrationFilter
7. customdry the collected solid under vacuum at 45° C
8. additionAdd the solid to ethyl acetate (400 mL)
9. temperatureheat the mixture
10. temperatureto reflux
11. temperatureThen cool to 22° C.
12. filtrationfilter the solid
13. additionAdd the wet solid to ethyl acetate (200 mL)
14. temperatureheat
15. temperatureto reflux for 30 min
16. temperatureCool the mixture to 22° C. over one hour
17. temperaturecool to 0-5° C. during 5 min
18. filtrationFilter the mixture
19. customdry the isolated solid under vacuum to constant weight

ORD record

ord-6ee2bc39c68744409e19df59cc987c15

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968587B2