Triethylamine → HCID 86728260, compound

Participants

Reaction Steps

To a solution of 5-(11-fluoro-6-(hydroxymethyl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (30 mg, 0.05 mmol, Compound 87, single enantiomer) and N-Boc-L-Valine (20 mg, 0.09 mmol) in dichloromethane, EDCI (20 mg, 0.10 mmol), DMAP (8 mg, 0.06 mmol) and Et3N (0.01 mL) were added. The reaction mixture was stirred at room temperature overnight. Then H2O was added, and extracted with dichloromethane. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified using prep-TLC (dichloromethane:MeOH=40:1) to provide (2S)-(11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate (30 mg, yield: 76%). 1H-NMR (CDCl3, 400 MHz) δ 7.98˜8.02 (m, 3H), 7.67 (s, 1H), 7.46˜7.54 (m, 2H), 7.19˜7.25 (m, 5H), 6.84˜6.89 (m, 1H), 6.62˜6.65 (m, 1H), 5.98 (br s, 1H), 4.91 (d, J=8.4 Hz, 1H), 4.42˜4.48 (m, 1H), 4.30˜4.35 (m, 1H), 4.18 (br s, 1H), 3.38 (s, 3H), 3.01 (d, J=4.8 Hz, 3H), 2.72 (s, 3H), 1.90˜1.95 (m, 1H), 1.45 (s, 9H), 0.88 (d, J=6.4 Hz, 3H), 0.79 (d, J=6.4 Hz, 3H). MS (M+H)+: 844.

Provenance & Evidence