Water → HCID 68838889, compound

HRID 2105765Notes

Reaction equation

HRID 2105765 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10]([CH3:16])=[C:11]([C:13]([OH:15])=O)[N:12]=1.CN(C(ON1[N:33]=[N:32][C:27]2C=[CH:29][CH:30]=[CH:31][C:26]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.NN1CCCCC1.O>CN(C=O)C>[N:32]1([NH:33][C:13]([C:11]2[N:12]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[NH:9][C:10]=2[CH3:16])=[O:15])[CH2:29][CH2:30][CH2:31][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 166581-AminopiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 434450792-(2-Chlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acid

Product 1

HCID 68838889HCID 68838889, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1 g of 2-(2-chloro-phenyl)-5-methyl-1H-imidazole-4-carboxylic acid in 10 ml of DMF was added 1.36 g of TBTU and 3.6 ml of Hünigs' base and the reaction mixture was stirred for 1 minute. Then 0.46 ml of 1-aminopiperidin was added and the reaction mixture was stirred for 1.5 hour at room temperature. After such time the reaction mixture was poured onto 200 ml of water and extracted with ethyl acetate (2×200 ml). The combined organic extracts were then washed with water (2×100 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo to yield an oil which crystallized on standing. The residue was then triturated with heptane, the solid was filtered and dried to yield 1.12 g of the title compound, MS (ISP) 319.0 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for 1.5 hour at room temperature
  2. extractionextracted with ethyl acetate (2×200 ml)
  3. washThe combined organic extracts were then washed with water (2×100 ml) and brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield an oil which
  7. customcrystallized
  8. customThe residue was then triturated with heptane
  9. filtrationthe solid was filtered
  10. customdried

Sources & evidence

ORD record
ord-c5072cb94aa34f1991817ea36b688898
Source dataset
uspto-grants-2009_08
Patent number
US07579369B2

Reaction notes

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