Chloro-N,N-diethylacetamide → HCID 89761686, compound

Participants

Reaction Conditions

Reaction Steps

To a flask charged with N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (INTERMEDIate M) (0.104 g, 0.25 mmol) was added DMF (0.7 ml), and cooled in an ice water bath prior to the addition of NaH (60% in mineral oil) (10 mg, 0.25 mmol). The mixture was stirred for 45 min at 0° C., then 30 min at room temperature. To a separate vial charged with 2-chloro-N,N-diethylacetamide (37 mg, 0.25 mmol) was added DMF (0.3 ml), then the solution of deprotonated amine. The resulting mixture was sealed and shaken at rt overnight. The mixture was quenched with the addition of MeOH, then dried under reduced pressure and purified with NH4OH modified RP-HPLC affording N,N-diethyl-2-(7-(N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3 H)-yl)acetamide (27.4 mg, 27%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.01 (t, J=7.05 Hz, 3 H) 1.18 (t, J=7.10 Hz, 3 H) 3.21-3.27 (m, 2 H) 3.36 (br. s., 2 H) 3.39-3.45 (m, 2 H) 4.18 (t, J=4.35 Hz, 2 H) 4.26 (s, 2 H) 6.49 (d, J=8.71 Hz, 1 H) 6.75 (d, J=4.35 Hz, 1 H) 7.00 (d, J=2.06 Hz, 1 H) 7.13 (dd, J=8.59, 2.06 Hz, 1 H) 7.19 (d, J=4.58 Hz, 1 H) 12.47 (br. s., 1 H). m/z (ESI) 411.1 (M+H)+.

Provenance & Evidence