Isocyanate → 2-[3-(3-Chloro-phenyl)-ureido]-N-[1-(3,4-dichloro-benzyl)-azetidin-3-ylmethyl]-acetamide

HRID 638809Notes

Reaction equation

HRID 638809 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].[N-:20]=[C:21]=[O:22]>CN(C)C=O.C(Cl)(Cl)Cl.CO>[Cl:18][C:15]1[CH:14]=[C:13]([NH:20][C:21](=[O:22])[NH:1][CH2:2][C:3]([NH:5][CH2:6][CH:7]2[CH2:10][N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=3)[CH2:8]2)=[O:4])[CH:12]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 105034IsocyanateHCID 687143682-Amino-N-[1-(3,4-dichloro-benzyl)-azetidin-3-ylmethyl]-acetamide

Product 1

HCID 115542912-[3-(3-Chloro-phenyl)-ureido]-N-[1-(3,4-dichloro-benzyl)-azetidin-3-ylmethyl]-acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×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 of the isocyanate (1.5 M equivalents) in dimethylformamide and left at room 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-9e2e0a558f5d4f7a88b0ebcc4ab7e169
Source dataset
uspto-grants-2010_04
Patent number
US07691841B2

Reaction notes

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