Methyl iodide → HCID 25030229, compound

HRID 2192677Notes

Reaction equation

HRID 2192677 reaction equation
[OH:1][C:2]1[N:6]=[CH:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[O:16])=[CH:10][CH:9]=2)[C:3]=1[C:27]([NH2:29])=[O:28].[C:30](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.[Cl-].[Na+].O>[CH3:30][O:1][C:2]1[N:6]=[CH:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[O:16])=[CH:10][CH:9]=2)[C:3]=1[C:27]([NH2:29])=[O:28]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25029510HCID 25029510, compound

Product 1

HCID 25030229HCID 25030229, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

200 mg (0.517 mmol) of 5-hydroxy-3-{4-[(naphthalene-1-carbonyl)amino]benzyl}-3H-imidazole-4-carboxamide are dissolved in 5 ml of dry DMF in a round-bottomed flask under argon. 285 mg (2.07 mmol; 4 eq.) of potassium carbonate are then added. After one hour at room temperature, 440 mg (3.1 mmol; 6 eq.) of methyl iodide are added. After stirring for 24 hours at room temperature, the reaction medium is poured into brine and a precipitate appears. After stirring for 20 minutes, the precipitate is filtered off and then washed with water. After drying, 72 mg of a white solid are obtained.

Workup

  1. stirringAfter stirring for 20 minutes
  2. filtrationthe precipitate is filtered off
  3. washwashed with water
  4. customAfter drying

Sources & evidence

ORD record
ord-6dcd69b79e0943c0962e127e1c8076b2
Source dataset
uspto-grants-2012_12
Patent number
US08329738B2

Reaction notes

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