Water → 1-Benzyl-4-benzylamino-6-trifluoromethyl-1,3-dihydro-imidazo[4,5-c]pyridine-2-one

HRID 639620Notes

Reaction equation

HRID 639620 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]([NH2:15])=[C:13]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[C:11]([C:24]([F:27])([F:26])[F:25])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.CCCCCCC.C[CH2:37][O:38]C(C)=O>CC(OC)(C)C>[CH2:17]([N:16]1[C:13]2[CH:12]=[C:11]([C:24]([F:27])([F:26])[F:25])[N:10]=[C:9]([NH:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:14]=2[NH:15][C:37]1=[O:38])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8900HeptaneHCID 67456850N2,N4-Dibenzyl-6-trifluoromethyl-pyridine-2,3,4-triamine

Product 1

HCID 674571721-Benzyl-4-benzylamino-6-trifluoromethyl-1,3-dihydro-imidazo[4,5-c]pyridine-2-one

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

N2,N4-Dibenzyl-6-trifluoromethyl-pyridine-2,3,4-triamine (9.02 g, 24.2 mmol) was dissolved in TBME (180 ml) and CDl (19.6 g, 121 mmol) was added. The reaction mixture was stirred at room temperature for 72 h. Water (100 ml) was added to the reaction mixture and the layers were separated. The aqueous was extracted with EtOAc (200 ml). The combined organics were washed with brine (50 ml), dried over MgSO4 and concentrated in vacuo to give the crude (25 g). Column chromatography through silica eluting with 30:70→60:40 Heptane:EtOAc gave the title compound (2.64 g) as a white fluffy solid.

Workup

  1. additionCDl (19.6 g, 121 mmol) was added
  2. customthe layers were separated
  3. extractionThe aqueous was extracted with EtOAc (200 ml)
  4. washThe combined organics were washed with brine (50 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give the crude (25 g)

Sources & evidence

ORD record
ord-b849caf7a44f4062a02a0d098c8f39da
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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