1,2-Dichloroethane → HCID 57812413, compound

Participants

Reaction Conditions

Reaction Steps

7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridin-6-ylamine (10.0 mg, 0.0237 mmol), tert-butyl 3-oxoazetidine-1-carboxylate (8.11 mg, 0.0474 mmol), sodium triacetoxyborohydride (25.1 mg, 0.118 mmol) and 1,2-dichloroethane (1.0 mL, 13 mmol) were mixed and stirred at 70° C. overnight. After extraction with DCM and water, the organic layer was dried and dissolved in DCM (1.0 mL, 16 mmol). TFA (1.0 mL, 13 mmol) was added at 0° C. The mixture was stirred at 0° C. for 1 hour. The crude was passed through SCX-2 SPE and product was released by 2 M NH3 in methanol for purification by the MDPS. MS (ES+): m/z 477.10/479.15 (100/80) [MH+]. HPLC: tR=0.57 min (HPLC-ACQUITY, Analytical). 1H NMR (400 MHz, CD3OD): δ=1.88 (d, J=6.8 Hz, 3H), 2.54 (br. s., 2H), 2.64-2.68 (m, 2H), 3.11-3.18 (m, 2H), 3.53 (t, J=6.9 Hz, 1H), 3.94-4.08 (m, 4H), 6.27 (br. s., 1H), 6.50 (q, J=7.0 Hz, 1H), 7.22 (t, J=8.6 Hz, 1H), 7.40 (dd, J=9.0, 4.9 Hz, 1H), 7.63 (s, 1H), 8.18 (s, 1H).

Provenance & Evidence