Water → HCID 18753037, compound

HRID 1838220Notes

Reaction equation

HRID 1838220 reaction equation
CI.NC1[CH:29]=[CH:28][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=3)[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])(C)[C:10]2=O)=[C:6]([O:30][CH3:31])[CH:5]=1.[C:32](=[O:35])([O-])[O-].[K+].[K+].O.[CH3:39][N:40]([CH3:43])[CH:41]=O>CO>[Cl:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:9]([CH2:8][C:7]1[CH:28]=[CH:29][C:41]([N:40]([CH3:43])[CH3:39])=[CH:5][C:6]=1[O:30][CH3:31])[C:32](=[O:35])[C:11]2([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[CH3:10]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15521770HCID 15521770, compound

Product 1

HCID 18753037HCID 18753037, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

150 ml of methyl iodide are added to 238 mg of the compound of Example 48, in 4 ml of methanol and 1 ml of dimethylformamide, and 100 mg of potassium carbonate and then the reaction mixture is heated at 45° C. for 24 hours. 10 ml of water are added at room temperature and extraction is carried out with ethyl acetate. The organic phase is washed twice with water and dried over anhydrous sodium sulphate, the solvents are evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, elution being carried out with a 90/10 (v/v) cyclohexane/ethyl acetate mixture. The residue obtained is crystallized from n-pentane, filtered off and dried under reduced pressure for 4 hours; M.p.=135° C.

Workup

  1. extractionextraction
  2. washThe organic phase is washed twice with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customthe solvents are evaporated under reduced pressure
  5. customthe residue is purified by chromatography on a column of silica gel, elution
  6. customThe residue obtained
  7. customis crystallized from n-pentane
  8. filtrationfiltered off
  9. customdried under reduced pressure for 4 hours

Sources & evidence

ORD record
ord-efc3ed34bce7441683a507d0456d768d
Source dataset
uspto-grants-2004_01
Patent number
US06673790B1

Reaction notes

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