Dimethyl Sulfate → HCID 178502861, compound

HRID 1364804Notes

Reaction equation

HRID 1364804 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([C:16](=[NH:19])[NH:17][OH:18])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.[OH-].[Na+].[CH3:29]OS(OC)(=O)=O>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:11]=[CH:12][C:13]([C:16](=[NH:19])[NH:17][O:18][CH3:29])=[CH:14][CH:15]=2)=[CH:4][C:3]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 178513318HCID 178513318, compound

Product 1

HCID 178502861HCID 178502861, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

100 mg of N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(N-hydroxycarbamimidoyl)benzamide was cooled to 0° C. in 1.5 mL of Dioxane. 5 mL of 2N NaOH was slowly added followed by dropwise addition of 33 μL of dimethylsulfate. The ice bath was removed and reaction was stirred at room temperature for 1 hour. The reaction was subsequently evaporated and extracted with water twice in Ethyl Acetate, dried with Magnesium Sulfate, filtered and concentrated to yield pure N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(N-methoxycarbamimidoyl)benzamide. MS (Q1) 381 (M)+.

Workup

  1. customThe ice bath was removed
  2. customreaction
  3. customThe reaction was subsequently evaporated
  4. extractionextracted with water twice in Ethyl Acetate
  5. dry with materialdried with Magnesium Sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3567d686ef2c4ecf841072201024da2c
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

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