2,5-Dimethoxytetrahydrofuran → HCID 178522092, compound

HRID 491805Notes

Reaction equation

HRID 491805 reaction equation
Cl.Cl.[NH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([NH:12][C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][C:14]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:11])[CH2:6][CH2:5]1.CO[CH:34]1[CH2:38][CH2:37][CH:36](OC)O1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[N:3]1([C@H:4]2[CH2:9][CH2:8][C@H:7]([C:10]([NH:12][C:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[O:15][C:14]=3[C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=3)=[O:23])=[O:11])[CH2:6][CH2:5]2)[CH:34]=[CH:38][CH:37]=[CH:36]1

Participants

5

Reactant 3

HCID 790982,5-Dimethoxytetrahydrofuran2×HCID 517045Sodium AcetateHCID 178478721HCID 178478721, compound

Product 1

HCID 178522092HCID 178522092, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Trans-3-(4-aminocyclohexylcarbonylamino)-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide dihydrochloride (200 mg) obtained in Example 219, tetrahydro-2,5-dimethoxyfuran (53 μl), sodium acetate (68 mg) are stirred at 80° C. for 2 hours in acetic acid (3 ml). To the mixture is added tetrahydro-2,5-dimethoxyfuran (26 μl), and the mixture is further stirred at 80° C. for 2 hours. After cooling, the reaction solution is poured into ice-water, and the mixture is extracted with chloroform. The organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution, a saturated brine, and 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/hexane=1/5→ethyl acetate/hexane=1/3) to give the title compound (96 mg).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materiala saturated brine, and dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate/hexane=1/5→ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-b14c34a8afc047dfa048208bc091a8b4
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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