Reaction #487576

Reaction equation

2-chloroethyl isocyanate

3-(4-aminopiperidin-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile

potassium carbonate

→

3-(4-aminopiperidin-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile

final product

1-(2-chloroethyl)-3-(1-(5-cyano-2-(3,5-dichlorophenoxy)-phenylsulfonyl)piperidin-4-yl)urea

Solvents

THF

Conditions

Workup

1. 1
   Otherthe starting material was consumed (confirmed by HPLC)
2. 2
   Filtrationthe mixture was filtered
3. 3
   Otherto remove potassium carbonate
4. 4
   ConcentrationThe resulting filtrate was concentrated in vacuo
5. 5
   Otherthe solid triturated with dichlormethane and isopropyl ether
6. 6
   Otherfitted
7. 7
   Otherto obtain a white powder (838 mg, 67% yield, 97% purity)

Procedure

3-(4-aminopiperidin-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile was prepared following the procedure of Example 1. The final product was prepared by dissolving 3-(4-aminopiperidin-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile (1.00 g) in THF (30 mL) followed by the addition potassium carbonate (975 mg, 3.0 eq.), then 2-chloroethyl isocyanate (496 mg, 2.0 eq.) dropwise. After stirring for 1 hour, the starting material was consumed (confirmed by HPLC), and the mixture was filtered to remove potassium carbonate. The resulting filtrate was concentrated in vacuo, the solid triturated with dichlormethane and isopropyl ether, and fitted to obtain a white powder (838 mg, 67% yield, 97% purity).

Source