Reaction #2329075

Reaction equation

5-(3,5-Dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-2-methyl-benzoic acid

1-aminomethyl-cycloheptanol HCl

EDCI

HCl

→

title compound

Yield 41.2%

5-(3,5-Dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-N-(1-hydroxy-cycloheptylmethyl)-2-methyl-benzamide

Yield 41.2%

Solvents

DMF

water

Conditions

Workup

1. 1
   ExtractionThe aqueous was extracted with CH2Cl2 (3×)
2. 2
   Washwashed with brine
3. 3
   Dryingdried over sodium sulfate
4. 4
   Concentrationconcentrated in vacuo
5. 5
   Otherto give a tan solid
6. 6
   OtherThe crude was recrystallized from CH2Cl2

Procedure

A slurry of 5-(3,5-Dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-2-methyl-benzoic acid (5.0 g, 20.2 mmol), 1-aminomethyl-cycloheptanol HCl (5.4 g, 30.3 mmol), EDCI (5.8 g), and DMAP (7.4 g, 60.6 mmol) in DMF (67.3 mL) was stirred at ambient temperature for 14 hours. The reaction was then poured into 1N HCl (50 mL) and diluted with water (15 fold). The aqueous was extracted with CH2Cl2 (3×). The organics were combined, washed with brine, dried over sodium sulfate, and concentrated in vacuo to give a tan solid. The crude was recrystallized from CH2Cl2 to give the title compound as an off-white solid (3.1 g).

Source