Benzylamine → HCID 66558332, compound

Participants

Reaction Steps

To a mixture of [2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]acetic acid trifluoroacetic acid salt (100 mg, 0.21 mmol), HATU (96 mg, 0.25 mmol) and NEt3 (63 mg, 0.63 mmol) in DMF (2 mL) was added a solution of benzylamine (27 mg, 0.25 mmol) in DMF (0.2 mL) and the resulting mixture stirred at RT for 3 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-8% tMeOH in DCM) affording 120 as a white solid (78 mg, 84%). LCMS: RT 3.94 min [M+H]+ 443.3. 1H NMR (CDCl3, 400 MHz): δ 8.38 (1H, d, J=2.31 Hz), 7.91 (1H, s), 7.75 (1H, s), 7.27-7.19 (6H, m), 7.04 (1H, d, J=8.36 Hz), 5.89-5.88 (1H, m), 5.79 (1H, s), 4.46-4.43 (6H, m), 3.68 (2H, s), 1.59 (6H, d, J=6.62 Hz)

Provenance & Evidence