Reaction #40481

Reaction equation

H2O

6-chloro-7-ethylsulfanyl-9H-β-carbolin-8-ylamine

2-methylnicotinic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

N-(6-chloro-7-ethylsulfanyl-9H-β-carbolin-8-yl)-2-methyl-nicotinamide

Yield 40.7%

Solvents

pyridine

MeOH

Conditions

Workup

1. 1
   Otherthe resulting reaction mixture
2. 2
   TemperatureNext, the reaction mixture was cooled to RT
3. 3
   Concentrationconcentrated
4. 4
   Otherto afford a brown, viscous syrup
5. 5
   OtherThe resulting precipitated solid
6. 6
   Filtrationwas collected via suction filtration
7. 7
   Washwashed with 1:1 hexanes/diethyl ether (2×20 ml)
8. 8
   Otherair-dried

Procedure

A 25 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-ethylsulfanyl-9H-β-carbolin-8-ylamine (37.2 mg, 0.13 mmol) and 2-methylnicotinic acid (36.2 mg, 0.26 mmol) in 3 ml anhydrous pyridine. To the resulting light-orange mixture at RT was added solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (73.2 mg, 0.38 mmol) and the resulting reaction mixture was heated to 80° C. for 5 days. Next, the reaction mixture was cooled to RT and concentrated to afford a brown, viscous syrup. The syrup was dissolved in a minimal amount of MeOH (˜2 ml), slowly added to a 5:1 mixture of H2O/saturated sodium bicarbonate (˜20 ml), and stirred at RT for 2.5 hr. The resulting precipitated solid was collected via suction filtration, washed with 1:1 hexanes/diethyl ether (2×20 ml), and air-dried to afford 21.0 mg of N-(6-chloro-7-ethylsulfanyl-9H-β-carbolin-8-yl)-2-methyl-nicotinamide as a tan solid (˜38%). LCMS (ammonium acetate standard method) retention time=2.33 min. (M+=397; M−=395).

Source