Dimethylformamide → N-[1-(3,4-Dichloro-benzyl)-azetidin-3-ylmethyl]-2-(4-methoxy-benzenesulfonylamino)-acetamide

HRID 638810Notes

Reaction equation

HRID 638810 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH2:6][CH:7]1[CH2:10][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:8]1)=[O:4].C(N([CH2:25][CH3:26])CC)C.[S:27](Cl)(Cl)(=[O:29])=[O:28].CN(C)[CH:34]=[O:35]>C(Cl)(Cl)Cl.CO>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[CH2:11][N:9]1[CH2:10][CH:7]([CH2:6][NH:5][C:3](=[O:4])[CH2:2][NH:1][S:27]([C:26]2[CH:25]=[CH:14][C:13]([O:35][CH3:34])=[CH:12][CH:11]=2)(=[O:29])=[O:28])[CH2:8]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 687143682-Amino-N-[1-(3,4-dichloro-benzyl)-azetidin-3-ylmethyl]-acetamide

Product 1

HCID 11655799N-[1-(3,4-Dichloro-benzyl)-azetidin-3-ylmethyl]-2-(4-methoxy-benzenesulfonylamino)-acetamide

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A solution of 2-Amino-N-[1-(3,4-dichloro-benzyl)-azetidin-3-ylmethyl]-acetamide (1 M equivalent) in dimethylformamide is treated with a solution triethylamine (3 M equivalents) followed by a solution of the sulphonyl chloride (1.5 M equivalents) in dimethylformamide and left at ambient temperature overnight. The reaction mixture is diluted with chloroform/methanol 50:50 and applied to a SCX-3 1 g cartridge. The cartridge is washed with chloroform methanol 50:50, and the compound eluted with a solution of 10% ammonia in methanol. The solvent is evaporated to afford the title compound.

Workup

  1. washThe cartridge is washed with chloroform methanol 50:50
  2. washthe compound eluted with a solution of 10% ammonia in methanol
  3. customThe solvent is evaporated

Sources & evidence

ORD record
ord-5546d9559b9342198e53d8a8397a0c75
Source dataset
uspto-grants-2010_04
Patent number
US07691841B2

Reaction notes

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