1,2-Dichloroethane → HCID 86629660, compound

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Reaction Steps

To a stirred solution of 4-trifluoromethylbenzoic acid (60.0 mg, 0.316 mmol) in anhydrous DMF (1.2 mL) at ambient temperature under nitrogen, add EDC (63.6 mg, 0.332 mmol), 1-hydroxybenzotriazole (44.8 mg, 0.332 mmol), 4-dimethylaminopyridine (40.5 mg, 0.332 mmol) and a solution of 6-(3-aminopropylthio)-3-tert-butoxycarbonyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (123 mg, 0.332 mmol) in DCM (2 mL). Stir for 18 h at ambient temperature. Add water, extract twice with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Treat the residue with trifluoroacetic acid (0.272 mL, 0.640 mmol) in DCM (0.451 mL) at ambient temperature for 18 h. Concentrate in vacuo and purify by preparative reverse phase HPLC [Column: YMC ODS-AQ 120 Å 20×250 mm [S10-20 μm]; eluent: 95:5 to 5:95 A/B; solvent A: water, 0.1% TFA, 1% isopropanol; solvent B: acetonitrile, 0.05% TFA, 1% isopropanol; flow rate 20 mL/min] to give the title compound as a white solid (31.0 mg, 18%). MS (APCI+) m/z 443 (M+H)+.

Provenance & Evidence