Hydrochloride methanol → HCID 71252734, compound

HRID 2411190Notes

Reaction equation

HRID 2411190 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:20]COC1CCCCO1)[C:7]1([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)=[O:5])C.Cl.CO>CO>[O:5]=[C:4]1[N:6]([C:7]2([C:10]3[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=3)[CH2:9][CH2:8]2)[CH2:20][CH2:1][O:3]1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 71252207HCID 71252207, compound

Product 1

HCID 71252734HCID 71252734, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(1-{ethoxycarbonyl-[2-(tetrahydropyran-2-yloxy)ethyl]amino}cyclopropyl)benzoate (128 mg) described in Preparation Example 68 was dissolved in methanol (4 mL), 5% hydrogen chloride/methanol was added under ice-cooling, and the mixture was stirred at room temperature for 3.5 hr. The solvent was evaporated from the reaction mixture, N,N-dimethylformamide (4 mL) and potassium carbonate (9 mg) were added, and the mixture was stirred at 140° C. for 6 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (53 mg).

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated from the reaction mixture, N,N-dimethylformamide (4 mL) and potassium carbonate (9 mg)
  3. additionwere added
  4. stirringthe mixture was stirred at 140° C. for 6 hr
  5. temperatureThe reaction mixture was cooled
  6. additionwater was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with water and saturated brine
  9. customthe solvent was evaporated
  10. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-89523596b6944349ad0acaa3363b476d
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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