Diisopropylethylamine → HCID 67089308, compound

Participants

Reaction Steps

A mixture of 3-fluoroisoquinoline-6-carboxylic acid (123 mg, 644 μmol)(prepared as shown in Scheme 23), HATU (245 mg, 644 μmol), and DIEA (122 μl, 698 μmol) in DMF (5 mL) was stirred at room temperature for 15 minutes. This mixture was added dropwise to a mixture of (R)-4-(tert-butoxycarbonylamino)-5-(6-(trifluoromethyl)pyridin-3-yl)pentanehydrazide (202 mg, 537 μmol) and DIEA (122 μL, 698 μmol) in DMF (5 mL), and the resulting mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 (20 mL) and DCM (20 mL). The layers were separated and the aqueous layer was extracted with DCM (2×20 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting white solid was recrystallized from EtOAc to deliver (R)—N′-(4-(tert-butoxycarbonylamino)-5-(6-(trifluoromethyl)pyridin-3-yl)pentanoyl)-3-fluoroisoquinoline-6-carbohydrazide (218 mg, 74%) as a white solid. LCMS (API-ES) m/z: 572.0 (M+Na+).

Provenance & Evidence