Sodium Iodide → HCID 19434954, compound

HRID 1736163Notes

Reaction equation

HRID 1736163 reaction equation
[C:1]([N:4]([C:9]1[C:33]([F:34])=[C:32]([NH:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[C:12]2[C:13](=[O:31])[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:19]([F:30])[CH:18]=3)[O:16][C:11]=2[C:10]=1[F:42])[CH2:5][CH2:6][CH2:7]Cl)(=[O:3])[CH3:2].[I-].[Na+].Cl.[CH3:46][NH:47][CH3:48].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:1]([N:4]([C:9]1[C:33]([F:34])=[C:32]([NH:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[C:12]2[C:13](=[O:31])[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:19]([F:30])[CH:18]=3)[O:16][C:11]=2[C:10]=1[F:42])[CH2:5][CH2:6][CH2:7][N:47]([CH3:48])[CH3:46])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 19434802HCID 19434802, compound

Product 1

HCID 19434954HCID 19434954, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

932 mg (1.54 mmol) of the above 7-[N-acetyl-N-(3-chloropropyl)amino]-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one was dissolved in 10 mL of dimethylformamide under argon atmosphere, 320 mg (7.68 mmol) of sodium iodide, 1.25 g (15.4 mmol) of dimethylamine hydrochloride and 2.12 g (15.4 mmol) of potassium carbonate were added and the mixture was stirred at 70° C. for 23 hours. Water was added to the reaction solution and the mixture was extracted twice with ethyl acetate. The organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform-chloroform:methanol:aqueous ammonia=40:1:1) to give 603 mg of 7-[N-acetyl-N-(3-dimethylaminopropyl)amino]-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one (yield: 64%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform-chloroform:methanol:aqueous ammonia=40:1:1)

Sources & evidence

ORD record
ord-1b135f6bace24f828f7b7e733ed9d105
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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