Potassium Carbonate → HCID 66716937, compound

Participants

Reaction Conditions

Reaction Steps

In a 4 mL screw cap vial, 2-methyl-6-(piperidin-4-yloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one 394E (0.054 g, 0.206 mmol), K2CO3 (0.142 g, 1.029 mmol), and 4-fluoro-N-methylbenzamide (0.038 g, 0.247 mmol) were suspended in DMSO (0.412 mL) to give a brown suspension. The reaction was stirred at 120° C. for 72 hr. The crude material was purified by prep HPLC-MS (40-75% MeCN in water). The fractions were collected and concentrated in vacuo affording the product as a tan solid (0.0186 g, 22.85% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34-1.47 (m, 3H) 1.59-1.74 (m, 2H) 1.93-2.07 (m, 2H) 2.71-2.82 (m, 3H) 3.09-3.23 (m, 2H) 3.61 (br. s., 2H) 4.38-4.50 (m, 1H) 4.58 (q, J=6.65 Hz, 1H) 4.68 (d, J=6.57 Hz, 1H) 6.50 (d, J=2.78 Hz, 1H) 6.53-6.62 (m, 1H) 6.67 (dd, J=8.72, 2.91 Hz, 1H) 6.88 (d, J=8.84 Hz, 1H) 6.94-7.06 (m, 2H) 7.71 (d, J=8.84 Hz, 2H) 7.81-7.88 (m, 1H) 8.10-8.20 (m, 1H) 10.57 (s, 1H). ESI-MS: m/z 396.3 (M+H)+.

Provenance & Evidence