1,2-Dichloroethane → HCID 86650849, compound

Participants

Reaction Steps

A suspension of 4-(6-chlorobenzo[d]thiazol-2-ylamino)benzoic acid (117 mg, 0.38 mmol), EDC (88 mg, 0.46 mmol) and HOBt (63 mg, 0.46 mmol) in a mixed solvent of DMF (1 mL) and CH2Cl2 (1 mL) was stirred for 5 min, and then ethyl 2-hydrazinylnicotinate (4A) (70 mg, 0.38 mmol) was added, followed by triethylamine (78 mg, 0.77 mmol). The mixture was stirred at room temperature for 2 h. Analysis by LC/MS indicated the starting material was not consumed. Additional EDC (20 mg, 0.1 mmol) and HOBt (15 mg, 0.11 mmol) were added, and the mixture stirred for another 2 h before quenching with water (3 mL). The resulting precipitate was isolated by filtration and triturated with MeOH to yield the title compound as a fluffy white solid (94 mg). The methanol solution was concentrated in vacuo to collect additional product (50 mg) (total 144 mg, 87% yield). HPLC/MS (Method C): retention time=2.23 min, [M+H]+=468.4.

Provenance & Evidence