1,2-Dichloroethane → 3-(1-(2-((5S)-2-(2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Participants

Reaction Steps

2-((5S)-2-(2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (319.0 mg, 0.685 mmol), 4,5-dihydro-3-(piperidin-4-yl)-1H-benzo[d][1,3]diazepin-2(3H)-one (336.1 mg, 1.370 mmol), EDC (262.6 mg, 1.370 mmol) and HOBT (209.8 mg, 1.370 mmol) were stirred at RT in DMF (4 mL) overnight. Transferred mixture to a separatory funnel with EtOAc and water. The aqueous layer was extracted with EtOAc (3×), the organic layers were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude was dissolved in DMSO and purified by reverse phase semi-prep chromatography (CH3CN/water mobile phase) to give 3-(1-(2-((5S)-2-(2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one. LC/MS: 692.34 (M+1) Rt=2.24 min (10-90% 3/5 min (gradient/run) w/formic acid).

Provenance & Evidence