Dimethylformamide → HCID 72311198, compound

HRID 1157951Notes

Reaction equation

HRID 1157951 reaction equation
[CH3:1][O:2][C:3](=[O:36])[N:4]=[C:5]([S:34][CH3:35])[C:6](=[N:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[C:20]([CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:19]=1)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]([OH:15])[C:8]=1[F:16].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:49][N:50]([CH3:54])[CH2:51][CH2:52]Cl>O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:36])[N:4]=[C:5]([S:34][CH3:35])[C:6](=[N:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[C:20]([CH2:25][NH:26][C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH:19]=1)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]([O:15][CH2:52][CH2:51][N:50]([CH3:54])[CH3:49])[C:8]=1[F:16]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate3×HCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride3×HCID 72311189HCID 72311189, compound

Product 1

HCID 72311198HCID 72311198, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of {2-[4-bromo-3-(t-butoxycarbonylaminomethyl)phenylimino]-2-(5-ethyl-2-fluoro-3-hydroxyphenyl)-1-methylsulfanylethylidene}carbamic acid methyl ester (542 mg) and DMF (21.6 mL) there were added potassium carbonate (257 mg) and 2-dimethylaminoethyl chloride hydrochloride (268 mg) at 0° C. in that order, under a nitrogen atmosphere. The mixture was stirred for 4 hours at 0° C., and then potassium carbonate (257 mg) and 2-dimethylaminoethyl chloride hydrochloride (268 mg) were again added in that order, stirring was continued for 4 hours at 0° C., and potassium carbonate (257 mg) and 2-dimethylaminoethyl chloride hydrochloride (268 mg) were added. The mixture was stirred overnight at room temperature, and then ethyl acetate (200 mL) and water (100 mL) were added. The mixture was sufficiently shaken, and then the organic layer was separated off, washed twice with water (100 mL) and once with saturated aqueous sodium chloride (100 mL) in that order, and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate system) to obtain the target compound (242 mg) as a colorless solid.

Workup

  1. stirringstirring
  2. waitwas continued for 4 hours at 0° C.
  3. stirringThe mixture was stirred overnight at room temperature
  4. stirringThe mixture was sufficiently shaken
  5. customthe organic layer was separated off
  6. washwashed twice with water (100 mL) and once with saturated aqueous sodium chloride (100 mL) in that order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe mixture was filtered
  9. customto obtain a filtrate
  10. distillationthe solvent in the filtrate was distilled off under reduced pressure
  11. customThe residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate system)

Sources & evidence

ORD record
ord-151014b169b449a1b8ef3998dad3a565
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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