Hydrochloric Acid → HCID 178474845, compound

HRID 491768Notes

Reaction equation

HRID 491768 reaction equation
[C:1]([N:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([NH:14][C:15]2[C:19]3[CH:20]=[C:21]([CH2:24][C:25](OC)=[O:26])[CH:22]=[CH:23][C:18]=3[O:17][C:16]=2[C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=2)=[O:30])=[O:13])[CH2:8][CH2:7]1)[CH3:5])(=[O:3])[CH3:2].[BH4-].[Li+].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]([N:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([NH:14][C:15]2[C:19]3[CH:20]=[C:21]([CH2:24][CH2:25][OH:26])[CH:22]=[CH:23][C:18]=3[O:17][C:16]=2[C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=2)=[O:30])=[O:13])[CH2:8][CH2:7]1)[CH3:5])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 178499403HCID 178499403, compound

Product 1

HCID 178474845HCID 178474845, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trans-3-[4-(N-acetyl-N-methylamino)cyclohexylcarbonylamino]-5-methoxycarbonylmethyl-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (2.95 g) obtained in Example 2 is suspended in tetrahydrofuran (65 ml), and thereto is added lithium borohydride (238 mg), and the mixture is stirred at room temperature for 12 hours. To the reaction solution is poured 10% hydrochloric acid under ice-cooling, and the mixture is stirred at room temperature for 15 minutes. Subsequently, the reaction solution is neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. 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=40/1), and the resulting residue is suspended in diethyl ether. The precipitates are collected by filtration to give the title compound (2.24 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for 15 minutes
  3. extractionextracted with ethyl acetate
  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. filtrationThe precipitates are collected by filtration

Sources & evidence

ORD record
ord-6694e9ce84e444f68951d2b8a651a6d5
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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