1-Hydroxybenzotriazole → HCID 68571184, compound

Participants

Reaction Steps

To a sol. of compound D5 (10 g, 14.7 mmol) in CH2Cl2 (200 mL) was added cyclopropyl-(2,3-dichlorobenzyl)amine (prepared by reductive amination from 2,3-dichlorobenzaldehyde and cyclopropylamine, 7.95 g, 36.8 mmol), DIPEA (10.1 mL, 58.8 mmol), DMAP (449 mg, 3.68 mmol), HOBt (2.48 g, 18.4 mmol), and EDC.HCl (8.45 g, 44.1 mmol). This mixture was stirred at rt for 3 days. EDC.HCl (2.83 g, 14.7 mmol) and DIPEA (2.5 mL, 26 mmol) were added, and the reaction mixture was stirred at rt for 24 h. EDC.HCl (2.82 g, 14.7 mmol) and cyclopropyl-(2,3-dichlorobenzyl)amine (3.10 g, 14.7 mmol) were added, and the mixture and was stirred for 48 h. CH2Cl2 was added, and the organic layer was washed with aq. 1M HCl (3×), and with aq. sat. NaHCO3 (1×). The org. layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:5→2:3) yielded the title compound (7.72 g, 65%). LC-MS: tR=1.31 min; ES+: 802.52.

Provenance & Evidence