Hydrochloric Acid → HCID 68592901, compound

HRID 1516620Notes

Reaction equation

HRID 1516620 reaction equation
FC(F)(F)C(O)=O.[OH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH2:14])=[NH:13].Br[CH2:19][CH2:20][O:21][C:22]([C:24]1[CH:46]=[CH:45][C:27]([O:28][CH:29]2[CH2:34][CH2:33][N:32](C(OCC3C=CC=CC=3)=O)[CH2:31][CH2:30]2)=[CH:26][CH:25]=1)=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.C(O)C.[C].[Pd]>[NH:32]1[CH2:31][CH2:30][CH:29]([O:28][C:27]2[CH:45]=[CH:46][C:24]([C:22]([O:21][CH2:20][CH2:19][O:8][C:9]3[CH:17]=[CH:16][CH:15]=[C:11]([C:12](=[NH:14])[NH2:13])[CH:10]=3)=[O:23])=[CH:25][CH:26]=2)[CH2:34][CH2:33]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 68593403HCID 68593403, compoundHCID 68594337HCID 68594337, compound

Product 1

HCID 68592901HCID 68592901, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3-Hydroxybenzamidine trifluoroacetate (298 mg, 1.19 mmol) obtained in Step 1 of Example 2, benzyl 4-{4-[(2-bromoethoxy)carbonyl]phenoxy}piperidine-1-carboxylate (500 mg, 1.08 mmol), and cesium carbonate (717 mg, 2.20 mmol) were suspended in dehydrated DMF, and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was ice-cooled, and 1N hydrochloric acid (4.5 ml) was added to the mixture and the mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate, and the mixture was washed with 0.1N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the obtained crude product (about 700 mg) was dissolved in ethanol (15 ml). 10% Palladium-carbon (105 mg) was added thereto, and the mixture was stirred for 5.5 hours under hydrogen atmosphere. After filtration through celite, the solvent was evaporated to give the title compound as a crude product. This compound in a crude state was used for the next reaction.

Workup

  1. temperaturecooled
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe obtained residue was diluted with ethyl acetate
  4. washthe mixture was washed with 0.1N hydrochloric acid and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained crude product (about 700 mg)
  8. stirringthe mixture was stirred for 5.5 hours under hydrogen atmosphere
  9. filtrationAfter filtration through celite
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-39cfe0e38c2b4d7e9513fefcef8ebb10
Source dataset
uspto-grants-2012_07
Patent number
US08227506B2

Reaction notes

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