Reaction #10897

Reaction equation

2-Bromo-1-[4-(1-pyrrolidinyl)phenyl]ethanone

1-(4-isothiocyanatophenyl)-4-methyl piperazine

1-(4-isothiocyanatophenyl)-4-methylpiperazine

cyanamide

Potassium t-butoxide

→

[4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl][4-(1-pyrrolidinyl) phenyl]methanone

Yield 4.0%

Solvents

acetonitrile

tert-Butanol

Conditions

Workup

1. 1
   workup.STIRRINGthe solution was stirred at room temperature for 2 days
2. 2
   FiltrationThe yellow-brown solid was filtered off
3. 3
   Washwashed with cold acetonitrile, water
4. 4
   OtherA portion of this crude product (50 mg) was purified by chromatography (10% methanol/dichloromethane)

Procedure

tert-Butanol (4 mL) and then 1-(4-isothiocyanatophenyl)-4-methyl piperazine (of Example 1; 219 mg, 1 mmol) were added to a solution of cyanamide (44 mg, 1.05 mmol) in acetonitrile (5 mL). Potassium t-butoxide (1 M in tert-butanol; 1 mL, 1 mmol) was added and the solution was stirred for 30 min. 2-Bromo-1-[4-(1-pyrrolidinyl)phenyl]ethanone (257 mg, 1 mmol) (Lancaster) was added, and the solution was stirred at room temperature for 2 days. The yellow-brown solid was filtered off and washed with cold acetonitrile, water and then cold acetonitrile (weight of solid: 271 mg). A portion of this crude product (50 mg) was purified by chromatography (10% methanol/dichloromethane) to give [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl][4-(1-pyrrolidinyl) phenyl]methanone (18.5 mg).

Source