Ethanol → HCID 68678014, compound

HRID 1725489Notes

Reaction equation

HRID 1725489 reaction equation
[Cl:1][C:2]1[C:3]([F:34])=[C:4]([CH:31]=[CH:32][CH:33]=1)[C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([N:22]=[C:23]3[N:27]([CH2:28][O:29][CH3:30])[CH:26]=[CH:25][S:24]3)[N:21]=2)[C:17]#[N:18])[CH2:9][CH2:8]1)=[O:6].[Cl-].O[NH3+:37].C(=O)([O-])[O-].[K+].[K+].[CH2:44]([OH:46])[CH3:45]>>[Cl:1][C:2]1[C:3]([F:34])=[C:4]([CH:31]=[CH:32][CH:33]=1)[C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[N:21]=[C:20]([N:22]=[C:23]3[N:27]([CH2:28][O:29][CH3:30])[CH:26]=[CH:25][S:24]3)[CH:19]=[C:16]([C:17]3[N:37]=[C:44]([CH3:45])[O:46][N:18]=3)[CH:15]=2)[CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 21645Hydroxylamine HClHCID 68680993HCID 68680993, compound

Product 1

HCID 68678014HCID 68678014, compound

Procedure

A mixture of 31.1 mg of 2-((4-(3-chloro-2-fluorobenzoyl)piperazin-1-yl)methyl)-6-((3-(methoxymethyl)-thiazol-2(3H)-ylidene)amino)isonicotinonitrile obtained in Example 104-(3), 13.0 mg of hydroxylammonium chloride, 17.2 mg of potassium carbonate and 3ml of ethanol was heated under reflux for 18 hours. The reaction solution was cooled to room temperature, and then concentrated. To the residue was added 3.0 ml of acetic anhydride followed by heating under reflux for 4 hours. The reaction solution was cooled to room temperature, and then concentrated. The reaction solution was diluted with chloroform and then washed with saturated potassium carbonate. The resulting organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated. The resulting residue was purified by a thin-layer chromatography for fractionation (eluent: chloroform/methanol=10/1) to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. concentrationconcentrated
  4. additionTo the residue was added 3.0 ml of acetic anhydride
  5. temperatureby heating
  6. temperatureunder reflux for 4 hours
  7. temperatureThe reaction solution was cooled to room temperature
  8. concentrationconcentrated
  9. additionThe reaction solution was diluted with chloroform
  10. washwashed with saturated potassium carbonate
  11. dry with materialThe resulting organic layer was dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationthe filtrate was concentrated
  14. customThe resulting residue was purified by a thin-layer chromatography for fractionation (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-eece328854444d2fbf2d75113fbf0bb0
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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