Hydrochloric Acid → HCID 58497420, compound

Participants

Reaction Conditions

Reaction Steps

(S)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-hexanoic acid (85 mg, 0.21 mmol) was dissolved in THF (1.0 mL) and CDI (76 mg, 0.47 mmol) was added at room temperature. The mixture was heated at 55° C. for 1 hour. After the mixture is cooled down to room temperature, 2-methyl-propane-2-sulfonic acid amide (57 mg, 0.42 mmol) was added and after 10 min, DBU (0.063 mL, 0.42 mmol) was added. The mixture was stirred for 16 hours at room temperature. Then 2.0 mL of 1.0 M HCl was added followed by 30 mL of water. The mixture is extracted with EtOAc (3×20 mL) and the organic layers were combined, dried and concentrated to give crude product. Purification first by flash column chromatography using 5% MeOH in CH2Cl2 then by preparative TLC (6% MeOH in CH2Cl2 with 1% concentrated NH4OH) afforded 79 mg (71%) of the title compound. LCMS, M++1, m/z: 526.13.

Provenance & Evidence