Tetrahydrofuran → HCID 22063804, compound

HRID 1828172Notes

Reaction equation

HRID 1828172 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[NH:13][C:14]([C:24](F)(F)F)=[N:15][C:16]=3[C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)=[CH:11][C:6]=2[N:5]([CH3:28])[C:4]1=[O:29])[CH3:2].CCN=C=NCCCN(C)C.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.C1C[O:50]CC1>CN(C=O)C>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[NH:13][C:14]([C:24]([N:41]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)=[O:50])=[N:15][C:16]=3[C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)=[CH:11][C:6]=2[N:5]([CH3:28])[C:4]1=[O:29])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 220639221-ethyl-3-methyl-5-(5-m-tolyl-2-trifluoromethyl-3H-imidazol-4-yl)-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 22063804HCID 22063804, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 1-ethyl-3-methyl-5-(5-m-tolyl-2-trifluoromethyl-3H-imidazol-4-yl)-1,3-dihydro-benzoimidazol-2-one (prepared as described above, 50 mg, 0.13 mmol), N,N-dimethylaminopyridine (48.7 mg, 0.40 mmol), EDCI (38.3 mg, 0.20 mmol) and morpholine (17.4 mg, 0.20 mmol) was stirred at room temperature in THF (1.33 mL) at room temperature. One drop of DMF was added to ensure solubility. The reaction mixture was allowed to stir overnight. The mixture was concentrated in vacuo, taken up in methylene chloride and washed with 10% aqueous citric acid. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo to afford a reddish-brown solid, which was recrystallized in diisopropyl ether to give 19 mg of the title compound. MS (M+1)=446.5.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washwashed with 10% aqueous citric acid
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford a reddish-brown solid, which
  6. customwas recrystallized in diisopropyl ether

Sources & evidence

ORD record
ord-f33bed92781240afb07925a94bdfafe7
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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