1,2-Dichloroethane → HCID 71556486, compound

Participants

Reaction Steps

To a flask was added a single enantiomer (S or R) of 3-((7-amino-5,6,7,8-tetrahydronaphthalen-1-yl)methyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (obtained through chiral separation of racemic 20-4) (15 mg, 0.029 mmol), then anhydrous HOBT (5.15 mg, 0.038 mmol), EDC (7.30 mg, 0.038 mmol), followed by NMP (1 ml), then ACETIC ACID (2.180 μl, 0.038 mmol) then DIPEA (0.025 ml, 0.143 mmol). The reaction mixture was stirred at room temperature (capped but not under N2) & followed by LC/MS for the disappearance of starting amine. The reaction mixture was diluted with MeOH/drops of H2O, was filtered (syringe filter), concentrated to desired volume (blow station) & submitted downstairs for mass guided reverse phase purification (TFA modifier); desired fractions concentrated to yield N-(8-((6-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-5-fluoro-2-oxobenzo[d]oxazol-3(2H)-yl)methyl)-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (22-1, S or R). HRMS [M+H] calculated; 518.0963, observed; 518.0937. 1H NMR (499 MHz, DMSO): presaturation at 3.35 ppm: δ 8.49 (s, 1H); 7.96 (d, J=7.5 Hz, 1H); 7.80 (d, J=5.4 Hz, 1H); 7.29 (d, J=9.6 Hz, 1H); 7.06 (d, J=4.5 Hz, 2H); 6.85-6.81 (m, 1H); 5.02-4.91 (m, 2H); 4.06-3.95 (m, 1H); 3.05-2.99 (m, 1H); 2.86-2.80 (m, 2H); 2.53-2.48 (m, 1H); 1.95-1.85 (m, 1H); 1.82 (s, 3H); 1.68-1.58 (m, 1H).

Provenance & Evidence