Water → HCID 10024171, compound

HRID 1983803Notes

Reaction equation

HRID 1983803 reaction equation
[CH:1]([N:4]([CH3:17])[C:5]1[NH:9][C:8]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:7]=2[N:6]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[F:25][C:26]([F:39])([F:38])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35](O)=[O:36])=[CH:29][CH:28]=1.O>CO.C(Cl)(Cl)Cl.[OH-].[Pd+2].[OH-].[C]>[CH:1]([N:4]([CH3:17])[C:5]1[NH:9][C:8]2[CH:10]=[C:11]([NH:14][C:35](=[O:36])[CH2:34][CH2:33][C:30]3[CH:29]=[CH:28][C:27]([C:26]([F:38])([F:39])[F:25])=[CH:32][CH:31]=3)[CH:12]=[CH:13][C:7]=2[N:6]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 35887363-(4-(Trifluoromethyl)phenyl)propionic AcidHCID 69844067N-Methyl-6-nitro-N-(propan-2-yl)-1H-benzimidazol-2-amine

Product 1

HCID 10024171HCID 10024171, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of said N-{2-[isopropyl(methyl)amino]-6-nitro-1H-benzimidazole (1.00 g) as obtained in Example 1-(1) in methanol (30 ml), 20% palladium hydroxide-carbon (200 mg) was added and stirred at room temperature under atmospheric pressure for 5 hours. The reaction solution was filtered through Celite, and the filtrate was condensed under reduced pressure. Thus obtained 6-amino-N-{2-isopropyl(methyl)amino]-1H-benzimidazole was dissolved in chloroform (15 ml), followed by successive addition of triethylamine (1.8 ml) and 3-[4-(trifluoromethyl)phenyl]propionic acid (930 mg) and dropwise addition, under cooling with ice, of 2-chloro-1,3-dimethyl-2-imidazolinium chloride (2M chloroform solution, 2.6 ml). After 15 hours' stirring at room temperature, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The organic layer was condensed under reduced pressure, the resultant residue was purified on silica gel column chromatography, (methanol/ethyl acetate=1/10) and washed with ether to provide the title compound (1.00 g).

Workup

  1. additionwas added
  2. filtrationThe reaction solution was filtered through Celite
  3. customcondensed under reduced pressure
  4. stirringAfter 15 hours' stirring at room temperature
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customcondensed under reduced pressure
  9. customthe resultant residue was purified on silica gel column chromatography, (methanol/ethyl acetate=1/10)
  10. washwashed with ether

Sources & evidence

ORD record
ord-5f56c109566944eebe2c707a3935f054
Source dataset
uspto-grants-2009_06
Patent number
US07541477B2

Reaction notes

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