Pyridine → HCID 87244831, compound

HRID 604938Notes

Reaction equation

HRID 604938 reaction equation
[ClH:1].[Br:2][C:3]1[CH:33]=[CH:32][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:31]=[CH:30][C:19]([O:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=4)=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=O)=[CH:5][CH:4]=1.N1C=CC=CC=1.Cl.[CH2:41]([O:43][NH2:44])[CH3:42]>C(O)C>[ClH:1].[Br:2][C:3]1[CH:4]=[CH:5][C:6](/[C:7](=[N:44]\[O:43][CH2:41][CH3:42])/[CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=4)=[CH:30][CH:31]=3)[CH2:11][CH2:10]2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 67038184HCID 67038184, compound

Product 1

HCID 87244831HCID 87244831, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound prepared in Example 5(15) (912 mg) in ethanol (10 mL) were added pyridine (5 mL) and O-ethylhydroxyamine hydrochloride (340 mg) and the solution was refluxed for 3 hours. After finishing the reaction, the reaction solution was concentrated. Water and 2N hydrochloric acid were added thereto and the solution was extracted with ethyl acetate. The organic layer was washed with brine and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate:methanol=25:1) and 4N hydrogen chloride/ethyl acetate solution was added to the obtained residue, which was concentrated to give the compound of the present invention (E-form: 409 mg, Z-form: 500 mg) having the following physical data.

Workup

  1. temperaturethe solution was refluxed for 3 hours
  2. customthe reaction
  3. concentrationthe reaction solution was concentrated
  4. additionWater and 2N hydrochloric acid were added
  5. extractionthe solution was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. concentrationconcentrated
  8. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate:methanol=25:1) and 4N hydrogen chloride/ethyl acetate solution
  9. additionwas added to the obtained residue, which
  10. concentrationwas concentrated
  11. customto give the compound of the present invention (E-form: 409 mg, Z-form: 500 mg)

Sources & evidence

ORD record
ord-9222a3b5591b477da9f27387f2106231
Source dataset
uspto-grants-2011_03
Patent number
US07910741B2

Reaction notes

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