Reaction #1528423

Reaction equation

Water

methyl iodide

2,4-dichloro-N-{[3-(cyclopropylmethyl)-1-(1H-1,2,3-triazol-4-ylsulfonyl)azetidin-3-yl]methyl}benzamide

potassium carbonate

→

title compound

2,4-dichloro-N-({3-(cyclopropylmethyl)-1-[(1-methyl-1H-1,2,3-triazol-4-yl)sulfonyl]azetidin-3-yl}methyl)benzamide

Solvents

DMF

Conditions

Workup

1. 1
   Otherthe residue azeotroped twice with toluene
2. 2
   OtherThe crude product was purified by preparative TLC on silica gel
3. 3
   Washeluted with 4% Methanol DCM

Procedure

To a stirred solution of 2,4-dichloro-N-{[3-(cyclopropylmethyl)-1-(1H-1,2,3-triazol-4-ylsulfonyl)azetidin-3-yl]methyl}benzamide (0.1 g; 0.23 mmol) in DMF (5 ml) at 0° C. was added potassium carbonate (0.062 g; 0.45 mmol) followed by methyl iodide (0.048 g; 0.021 ml; 0.34 mmol) and the solution stirred for 18 hours at ambient temperature. LC/MS shows three new products of identical mass ion m/e=458:460 (3:2). Water (1 ml) was added, the solvent stripped at reduced pressure, and the residue azeotroped twice with toluene. The crude product was purified by preparative TLC on silica gel eluted with 4% Methanol DCM to give the title compound as the most polar isomer (24 mg).

Source