Water → HCID 44591700, compound

HRID 1441241Notes

Reaction equation

HRID 1441241 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([CH2:20][CH:21]2[CH2:23][CH2:22]2)[CH2:11][N:10]([S:12]([C:15]2[N:16]=[N:17][NH:18][CH:19]=2)(=[O:14])=[O:13])[CH2:9]1)=[O:5].[C:29](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([CH2:20][CH:21]2[CH2:22][CH2:23]2)[CH2:9][N:10]([S:12]([C:15]2[N:16]=[N:17][N:18]([CH3:29])[CH:19]=2)(=[O:13])=[O:14])[CH2:11]1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522753HCID 178522753, compound

Product 1

HCID 44591700HCID 44591700, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. customthe residue azeotroped twice with toluene
  2. customThe crude product was purified by preparative TLC on silica gel
  3. washeluted with 4% Methanol DCM

Sources & evidence

ORD record
ord-f083e479b9b64d78a60b4b70c91f43a4
Source dataset
uspto-grants-2010_02
Patent number
US07655644B2

Reaction notes

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