Triethylamine → HCID 178457501, compound

HRID 491799Notes

Reaction equation

HRID 491799 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[C:18]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=2)=[O:27])=[O:10])[CH2:5][CH2:4]1.C(N([CH2:41][CH3:42])CC)C.[C:43](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl.CC(C)=O>[ClH:35].[CH3:24][N:23]([CH3:25])[C:21]([C:18]1[CH:19]=[CH:20][C:15]2[O:14][C:13]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)=[O:27])=[C:12]([NH:11][C:9]([C@H:6]3[CH2:7][CH2:8][C@H:3]([NH:2][CH:41]([CH3:42])[CH3:43])[CH2:4][CH2:5]3)=[O:10])[C:16]=2[CH:17]=1)=[O:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178484422HCID 178484422, compound

Product 1

HCID 178457501HCID 178457501, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

Trans-3-(4-aminocyclohexylcarbonylamino)-5-dimethylaminocarbonyl-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide hydrochloride (160 mg) obtained in Example 344 is suspended in dichloromethane (8 ml), and thereto are added successively triethylamine (129 μl), acetone (113 μl), and sodium triacetoxy borohydride (130 mg) under ice-cooling, and the reaction solution is warmed to room temperature, and stirred for 17 hours. Under ice-cooling, to the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is washed with a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate, then chloroform/methanol=30/1). The resulting residue is dissolved in ethanol, and thereto is added 4N hydrogen chloride in ethyl acetate. The reaction solution is concentrated and the resulting residue is suspended in diethyl ether. The precipitates are collected by filtration to give the title compound (94 mg).

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling, to the reaction solution
  3. extractionthe mixture is extracted with chloroform
  4. washThe organic layer is washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe resulting residue is purified by NH-silica gel column chromatography (eluent
  8. dissolutionThe resulting residue is dissolved in ethanol
  9. additionis added 4N hydrogen chloride in ethyl acetate
  10. concentrationThe reaction solution is concentrated
  11. filtrationThe precipitates are collected by filtration

Sources & evidence

ORD record
ord-65390d94aa724c32ab07c0fb4dbab570
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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