Dimethylformamide → HCID 69597599, compound

HRID 1796809Notes

Reaction equation

HRID 1796809 reaction equation
CN(C)C=O.[CH3:6][NH:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:12]([C:26]23[O:33][CH2:32][C:29]([CH3:34])([CH2:30][O:31]2)[CH2:28][O:27]3)[CH:11]1[CH3:35])=[O:9].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:43][C:44]1[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=1[CH3:51]>C(OCC)(=O)C>[CH3:6][NH:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:43][C:44]3[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=3[CH3:51])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:12]([C:26]23[O:33][CH2:32][C:29]([CH3:34])([CH2:28][O:27]2)[CH2:30][O:31]3)[CH:11]1[CH3:35])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27746055-Fluoro-2-methylbenzyl bromideHCID 69597610HCID 69597610, compound

Product 1

HCID 69597599HCID 69597599, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a N,N-dimethylformamide (1.5 ml) solution of 4-(4-Hydroxy-benzenesulfonyl)-2-methyl-3-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-piperazine-1-carboxylic acid methylamide (compound of formula XLV, 0.31 g, 0.7 mmol) was added cesium carbonate (0.45 g) and 2-bromomethyl-4-fluoro-1-methyl-benzene (0.214 g, 1.05 mmol). The reaction mixture was stirred at about 45° C. for about 16 hours and then was allowed to cool and was diluted with ethyl acetate and washed with water. The organic layer was dried with sodium sulfate and concentrated in vacuo to give 0.377 g of a compound of formula XLIV.

Workup

  1. temperatureto cool
  2. washwashed with water
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa88237a17f14c83b18183d5449495c2
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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