(R)-5-bromo-2-oxo-3-(1-phenylethyl)-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide → HCID 117629625, compound

Participants

Reaction Conditions

Reaction Steps

Into a solution of (R)-5-bromo-2-oxo-3-(1-phenylethyl)-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (38-1, 80 mg, 0.166 mmol, prepared from 35-3 by a reaction sequence analogous to that described herein) in NMP (831 ul) was added diethylzinc (1M in hexanes, 0.499 mmol) followed by chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (7 mg, 8.9 umol). The reaction vessel was sealed and heated to 120° C. for 12 h, cooled to rt, diluted with 1 ml of H2O and 3 ml of EtOAc, filtered through celite, concentrated and purified by reversed phase HPLC (2 cm×5 cm C18, acetonitrile-water gradient, 0.05% TFA added) to yield 5-ethyl-2-oxo-3-[(1R)-1-phenylethyl]-N-1,2,4-thiadiazol-5-yl-2,3-dihydro-1,3-benzoxazole-6-sulfonamide (38-2). 1H NMR (499 MHz, DMSO): δ 8.44 (s, 1H); 7.75 (s, 1H); 7.46 (d, J=7.7 Hz, 2H); 7.36-7.38 (m, 3H); 7.06 (s, 1H); 5.63 (d, J=7.3 Hz, 1H); 2.92-2.94 (m, 2H); 1.88 (d, J=7.1 Hz, 3H); 1.09 (t, J=7.4 Hz, 3H). LRMS C19H18N404S2 [M+H] calc 431.1, obs 431.0.

Provenance & Evidence