Acetate → HCID 67344136, compound

HRID 1673515Notes

Reaction equation

HRID 1673515 reaction equation
[C:1](O)(=O)C.C(N)=N.C([O-])(=O)C.COCCO.[NH2:17][C:18]1[CH:46]=[CH:45][CH:44]=[CH:43][C:19]=1[NH:20][C:21]1[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:23]([NH:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:22]=1>O.C(OCC)(=O)C>[C:35]([NH:34][C:23]1[CH:22]=[C:21]([N:20]2[C:19]3[CH:43]=[CH:44][CH:45]=[CH:46][C:18]=3[N:17]=[CH:1]2)[CH:33]=[CH:32][C:24]=1[C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])(=[O:42])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 175AcetateHCID 80192-MethoxyethanolHCID 160693Formamidine acetateHCID 67343432HCID 67343432, compound

Product 1

HCID 67344136HCID 67344136, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

28 mg of formamidine acetate was acetate to 1.0 mL of ethylene glycol monomethyl ether solution containing 44 mg of tert-butyl 4-(2-aminoanilino)-2-(benzamido)benzoate at room temperature and stirred at 80° C. for 3 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=1:1] to obtain 36 mg of tert-butyl 2-(benzamido)-4-(1H-benzimidazol-1-yl)benzoate as pale yellow oil.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with a saturated sodium hydrogen carbonate aqueous solution
  5. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=1:1]

Sources & evidence

ORD record
ord-b89b71cd05284b74acd814b8132e7b9d
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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