Methyl iodide → HCID 19434922, compound

HRID 1736147Notes

Reaction equation

HRID 1736147 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:27])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:14]([F:26])[CH:13]=3)[O:11][C:6]=2[C:5]([F:28])=[CH:4][C:3]=1[F:29].[H-].[Na+].I[CH3:33].[Cl-].[NH4+]>CN(C)C=O>[NH2:1][C:2]1[C:7]2[C:8](=[O:27])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH3:33])=[C:14]([F:26])[CH:13]=3)[O:11][C:6]=2[C:5]([F:28])=[CH:4][C:3]=1[F:29]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 19434972HCID 19434972, compound

Product 1

HCID 19434922HCID 19434922, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.99 g (4.73 mmol) of Compound 51 obtained in Example 51 was dissolved in 80 ml of dimethylformamide under argon atmosphere, 212 mg. of sodium hydride (60% oil disperison) and 0.60 ml of iodomethane were added and the mixture was stirred at room temperature for 1 hour. An aqueous saturated solution of ammonium chloride was added to the reaction solution, the precipitated crystals were collected by filtration and dissolved in ethanol, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give 2.09 g of 5-amino-2-[4-[N-(tert-butoxycarbonyl)-N-methylamino]-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. dissolutiondissolved in ethanol
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-9f94627440b14c3e95b2c210e4f379c5
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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