N-Methylbenzylamine → HCID 19365588, compound

HRID 1600065Notes

Reaction equation

HRID 1600065 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:33][C:13]3[N:14]([CH2:24][C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[CH:15]=[C:16]([S:19]([CH:21]([CH3:23])[CH3:22])=[O:20])[C:17](=[O:18])[C:12]=3[C:11]=2[CH2:34]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:36][NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:33][C:13]3[N:14]([CH2:24][C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[CH:15]=[C:16]([S:19]([CH:21]([CH3:23])[CH3:22])=[O:20])[C:17](=[O:18])[C:12]=3[C:11]=2[CH2:34][N:37]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:36])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 19365541HCID 19365541, compound

Product 1

HCID 19365588HCID 19365588, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (1.04 g, 1.8 mmol) obtained in Example 18 was dissolved in dimethylformamide (70 ml). To the solution was added diisopropylaminoethyl(1.15 g, 8.9 mmol) and N-methylbenzylamine (0.54 g, 4.5 mmol) at room temperature, and the mixture was further stirred for one hour. The reaction mixture was concentrated to dryness, and the residue was partitioned between ethyl acetate (300 ml) and water. The aqueous layer was extracted with ethyl acetate (100 ml), the extracts were combined, washed with an aqueous sodium chloride solution, dried with Na2 SO4, and the solvent was distilled off. Thus obtained residue was purified by silica gel column chromatography to give a solid form (1.09 g), and recrystallization from dichloromethane-ether-n-hexane gave pale yellow crystals (1.03 g, 93%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was partitioned between ethyl acetate (300 ml) and water
  3. extractionThe aqueous layer was extracted with ethyl acetate (100 ml)
  4. washwashed with an aqueous sodium chloride solution
  5. customdried with Na2 SO4
  6. distillationthe solvent was distilled off
  7. customThus obtained residue was purified by silica gel column chromatography
  8. customto give
  9. customa solid form (1.09 g), and recrystallization from dichloromethane-ether-n-hexane

Sources & evidence

ORD record
ord-2bc27f7566f745e9b0aa89f88aef4122
Source dataset
uspto-grants-1998_04
Patent number
US05744479

Reaction notes

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