Tartrate → HCID 131732905, compound

Participants

Reaction Steps

A procedure similar to Step C of Example 14 was used to couple 5-(4-chlorophenyl)-2,5-ethano-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1H-2-benzoazepine from Step B of Example 14 with 6-bromo-3,3a-dihydrobenzo[d]oxazol-2(7aH)-one. The desired coupling product was obtained and converted to the corresponding L-tartrate salt as in Step C to provide 64544-chlorophenyl)-2,5-ethano-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)-3,3a-dihydrobenzo[d]oxazol-2(7aH)-one, L-tartrate salt (34 mg, 11%, AUC HPLC >99%) as an off-white solid: 1H NMR (CD3OD, 500 MHz) δ 7.55 (s, 1H), 7.48-7.45 (m, 3H), 7.42 (dd, J=8.5, 2.0 Hz, 1H), 7.38-7.35 (m, 3H), 7.13 (d, J=8.5 Hz, 1H), 6.45 (d, J=8.5 Hz, 1H), 4.91 (s, 2H), 4.43 (s, 2H), 3.68-3.61 (m, 2H), 3.48-3.41 (m, 2H), 2.82-2.78 (m, 2H), 2.49-2.43 (m, 2H); ESI MS m/z 417 [M+H]+. Anal. Calcd. For C25H21ClN2O2.C4H6O6.3H2O: C, 56.09; H, 5.36; N, 4.51. Found: C, 56.42; H, 5.09; N, 4.29.

Provenance & Evidence