Piperidine → 2-(2-Piperidin-1-ylmethyl-1H-indol-6-yloxy)-thiazolo[4,5-b]pyridine

To a suspension of 6-(thiazolo[4,5-b]pyridin-2-yloxy)-1H-indole-2-carbaldehyde (76 mg, 0.26 mmol) in DCM (3 mL) was added piperidine (0.05 mL, 43 mg, 0.51 mmol), Na(OAc)3BH (65 mg, 0.31 mmol) and the reaction mixture was stirred (rt, 12 h). The reaction mixture was partitioned between saturated NaHCO3 (10 ml) and DCM (20 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×25 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by reverse phase HPLC to provide the title compound as a colorless solid (12 mg, 13%). MS (ESI): mass calcd. for C20H20N4OS, 364.1; m/z found, 365.1 [M+H]+. 1H NMR (500 MHz, CDCl3/CD3OD, 10/1): 8.51 (d, J=4.8, 1H), 7.97 (d, J=7.9, 1H), 7.54 (d, J=8.5, 1H), 7.40 (s, 1H), 7.18 (dd, J=7.9, 4.9, 1H), 7.02 (d, J=8.5, 1H), 6.36 (s, 1H), 3.63 (s, 2H), 2.53-2.47 (m, 2H), 2.47-2.36 (m, 2H), 1.76-1.44 (m, 6H).

1. customThe reaction mixture was partitioned between saturated NaHCO3 (10 ml) and DCM (20 mL)
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with DCM (2×25 mL)
4. customThe organic layer was dried
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe resulting residue was purified by reverse phase HPLC

ORD record

ord-51f9dc061c83410fa3ec6629f9e9c57d

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399465B2