Water → HCID 69020706, compound

HRID 229856Notes

Reaction equation

HRID 229856 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:18]([OH:20])=O.CN(C(ON1[N:37]=[N:36][C:31]2C=[CH:33][CH:34]=[CH:35][C:30]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.NN1CCCCC1.O>CN(C=O)C>[N:36]1([NH:37][C:18]([C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([O:13][C:14]([F:15])([F:17])[F:16])=[CH:11][CH:12]=3)[NH:6][C:2]=2[CH3:1])=[O:20])[CH2:33][CH2:34][CH2:35][CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 166581-AminopiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 534044015-Methyl-2-[4-(trifluoromethoxy)phenyl]-1H-imidazole-4-carboxylic acid

Product 1

HCID 69020706HCID 69020706, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1 g of 5-methyl-2-(4-trifluoromethoxy-phenyl)-1H-imidazole-4-carboxylic acid in 50 ml of DMF was added 1.12 g of TBTU and 3.0 ml of Hünigs' base and the reaction mixture was stirred for 1 minute. Then 0.38 ml of 1-aminopiperidine (as R1R2NH) was added and the reaction mixture was stirred for 4.5 hour at room temperature. After such time the reaction mixture was poured onto 250 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 after filtration, concentrated in vacuo to yield an oil which crystallized during concentration. The residue (about 30 ml volume) was then treated with heptane (200 ml), the solid was filtered and dried to yield 1.15 g of the title compound, MS (ISP) 369.0 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for 4.5 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. filtrationafter filtration
  6. concentrationconcentrated in vacuo
  7. customto yield an oil which
  8. customcrystallized during concentration
  9. additionThe residue (about 30 ml volume) was then treated with heptane (200 ml)
  10. filtrationthe solid was filtered
  11. customdried

Sources & evidence

ORD record
ord-651cc71e95d44cc99a19c6e2bfd581f8
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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