Hydrochloric Acid → HCID 178522096, compound

HRID 1820922Notes

Reaction equation

HRID 1820922 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:35]=[CH:34][C:33]([CH2:36][C:37](OC)=[O:38])=[CH:32][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1.[BH4-].[Li+].Cl.C(=O)([O-])O.[Na+]>O1CCCC1CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][OH:38])=[CH:32][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 178499402HCID 178499402, compound

Product 1

HCID 178522096HCID 178522096, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

Methyl [2-{[(5-chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(pyrrolidin-1-ylcarbonyl)cyclohexyl]carbonyl}-amino)benzofuran-5-yl]acetate (113 mg) obtained in Example 2 is suspended in tetrahydrofuran-ethanol (6:1) (7 ml). To the suspension is added lithium borohydride (13 mg), and the mixture is stirred at room temperature for 4 hours. After pouring 10% hydrochloric acid under ice-cooling, the reaction solution is stirred at room temperature for several minutes. The reaction solution is then basified by addition of a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate, and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform), and the resulting residue is then suspended in diethyl ether. The precipitates are collected by filtration and dried to give the title compound (28 mg). APCI-MS M/Z:539/541[M+H]+

Workup

  1. temperaturecooling
  2. stirringthe reaction solution is stirred at room temperature for several minutes
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer is washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure
  8. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform)
  9. filtrationThe precipitates are collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-62aaed33a17a4a8693afee8232151f3e
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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