Benzylethanolamine → 2-Chloro-N-[(1R,2R)-1-({[(2-hydroxyethyl)(phenylmethyl)amino]acetyl}amino)-2,3-dihydro-1H-inden-2-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide

Participants

Reaction Steps

2-(Benzylamino)ethanol (160 mg, 1.06 mmol) was added to a solution of 2-chloro-N-{(1R,2R)-1-[(chloroacetyl)amino]-2,3-dihydro-1H-inden-2-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 23; 216 mg, 0.53 mmol) and Et3N (500 μL, 3.60 mmol) in anhydrous THF (5 mL) and the reaction stirred for approximately 16 hours at room temperature then for a further 16 h at 50° C. The volatiles were removed under reduced pressure, the residue dissolved in EtOAc (10 mL), washed with H2O (2×10 mL) and dried (MgSO4). The solvent was removed under reduced pressure, the residue triturated (EtOAc:isohexane, 1:5), collected by filtration, washed with isohexane (10 mL) and dried to give the title compound (100 mg, 36%) as a brown solid.

Provenance & Evidence