Triethylamine → HCID 58997009, compound

Participants

Reaction Steps

To a stirred suspension of 3,5-dichloro-isonicotinic acid (85 mg, 0.44 mmol) in CH2Cl2 (3 mL) was added DMF (1 drop) and oxalyl chloride (0.12 mL, 1.4 mmol). The suspension was stirred at room temperature for 2 h, then concentrated under reduced pressure. A solution of (5-aminomethyl-2-{[(3-amino-pyridin-2-ylmethyl)-((S)-5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-phenyl)-methanol (88 mg, 0.22 mmol) in THF (3 mL) was added to the acid chloride followed by Et3N (0.04 mL, 0.3 mmol). The mixture was stirred for 1 h, then diluted with CH2Cl2 (10 mL) and washed with water (10 mL). The aqueous layer was extracted with CH2Cl2 (3×8 mL), and the combined organic layers were washed with saturated NaHCO3 (20 mL), then dried (Na2SO4) and concentrated under reduced pressure. The residue was purified using flash chromatography on silica gel (97:2:1 CH2Cl2/MeOH/NH4OH) to give COMPOUND 407 (21 mg, 17%), as a white foam.

Provenance & Evidence