Triethylamine → HCID 49780577, compound

Participants

Reaction Steps

Intermediate 42 (200 mg, 0.7 mmol) was dissolved in DCM (7 mL) and triethylamine (100 μL, 0.7 mmol) added followed by 5-(dimethylamino)-1-naphthalenesulfonyl chloride (207 mg, 0.77 mmol). The reaction was evaporated, reconstituted in EtOAc and washed with 1N HCl and 1N K2CO3. Flash chromatography eluted with 2:1 EtOAc:hexanes afforded compound 59 (338 mg, 93%) as a tan solid: Mp 102-107° C. 1H NMR (500 MHz, DMSO-d6□ 8.52 (d, J=8.5 Hz, 1H), 8.45 (s, 1H), 8.28 (d, J=8.7 Hz, 1H), 8.14 (d, J=7.3 Hz, 1H), 7.67 (t, J=7.5 Hz, 1H), 7.62 (t, J=8.1 Hz, 1H), 7.43 (d, J=9.1 Hz, 2H), 7.28 (d, J=7.5 Hz, 1H), 7.19 (d, J=8.7 Hz, 2H), 6.24 (d, J=7.5 Hz, 1H), 3.60-3.53 (m, 3H), 2.88 (t, J=10.5 Hz, 2H, obscured by s δ 2.84), 2.84 (s, 6H), 1.84 (dd, J=12.9, 3.0 Hz, 2H), 1.38 (dq, J=10.6, 3.6 Hz, 2H). Purity 97%. HRMS calculated for C25H27F3N4O4S+H+ 537.1783. found (ESI(+), [M+H]) 537.1785.

Provenance & Evidence