Reaction #40478

Reaction equation

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

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

Intermediate 28

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

2-methylnicotinic acid

H2O

→

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

Yield 89.5%

Solvents

MeOH

pyridine

Conditions

Workup

1. 1
   OtherTo the resulting reaction mixture at RT
2. 2
   TemperatureThe resulting mixture was cooled to RT
3. 3
   Concentrationconcentrated (rotavap)
4. 4
   Otherto afford a brown residue
5. 5
   FiltrationThe precipitated solid was collected via suction filtration
6. 6
   Washwashed with Et2O (2×150 ml)
7. 7
   Otherair-dried

Procedure

A 250 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-methylsulfanyl-9H-β-carbolin-8-ylamine (Intermediate 28, 2.336 g, 8.86 mmol) and 2-methylnicotinic acid (3.219 g, 23.4 mmol) in 80 ml anhydrous pyridine. To the resulting reaction mixture at RT was added solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7.080 g, 36.9 mmol) and the reaction mixture was heated to 100° C. (oil bath) for 2 days. The resulting mixture was cooled to RT and concentrated (rotavap) to afford a brown residue. The residue was redissolved in MeOH (50 ml), slowly added to a stirring mixture of 5:1 H2O/saturated aqueous sodium bicarbonate (600 mlL) and stirred at RT for ˜18 hr. The precipitated solid was collected via suction filtration, washed with Et2O (2×150 ml), and air-dried to afford 3.036 g of crude N-(6-chloro-7-methylsulfanyl-9H-β-carbolin-8-yl)-2-methyl-nicotinamide as a brown solid. The crude material was purified via HPLC (yields=˜40-60%)

Source