Diisopropylethylamine → HCID 178521637, compound

To an emulsion of cis-3-aminocyclobutanol hydrochloride (1.254 g, 10.15 mmol) in DCM (15 mL) was added MeOH (60 mL), imidazo[1,2-a]pyridine-8-carbaldehyde (1.5 g, 10.26 mmol) and DIPEA (2 mL, 11.45 mmol) and the reaction mixture stirred at room temperature under nitrogen for 10 minutes. Sodium triacetoxyborohydride (5.4 g, 25.5 mmol) was then added and the reaction mixture stirred under nitrogen for 18 hours and then concentrated in vacuo. The residue was dissolved in DCM (200 mL), aqueous sodium hydroxide (2M, 200 mL) was added and the mixture was stirred at room temperature for 1 hour. The layers were separated and to the aqueous phase was added sodium hydroxide pellets (ca. 5 g) which was then extracted with 3:1 chloroform:isopropanol (2×500 mL). The combined organic extracts were dried using a hydrophobic frit, evaporated in vacuo and the residue was dissolved in DCM and purified on a silica cartridge (100 g) using a 0-25% methanol-DCM gradient over 60 min. The product containing fractions were combined and evaporated in vacuo to give the title compound as an orange oil (2.3 g).

1. stirringthe reaction mixture stirred under nitrogen for 18 hours
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in DCM (200 mL)
4. additionaqueous sodium hydroxide (2M, 200 mL) was added
5. stirringthe mixture was stirred at room temperature for 1 hour
6. customThe layers were separated and to the aqueous phase
7. additionwas added sodium hydroxide pellets (ca. 5 g) which
8. extractionwas then extracted with 3:1 chloroform
9. customThe combined organic extracts were dried
10. customevaporated in vacuo
11. dissolutionthe residue was dissolved in DCM
12. custompurified on a silica cartridge (100 g)
13. customover 60 min
14. additionThe product containing fractions
15. customevaporated in vacuo

ORD record

ord-a0b6a3e5da3a47ecb14a1f130111d92a

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754101B2