Dimethyl Sulfate → HCID 178502861, compound

HRID 633178Notes

Reaction equation

HRID 633178 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-2a32ec4e1da24f1aa2920b7744bf7641
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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