Hydrochloric Acid → HCID 11524651, compound

HRID 1446531Notes

Reaction equation

HRID 1446531 reaction equation
C(O[C:4](=[O:25])/[C:5](=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]2)=[C:13]([O:23][CH3:24])[CH:12]=1)/[CH2:6][CH2:7][CH2:8]Cl)C.[NH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[N:29]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.CN(C=O)C.O>[Cl:34][C:30]1[N:29]=[C:28]([CH2:27][N:26]2[CH2:8][CH2:7][CH2:6]/[C:5](=[CH:10]\[C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]4)=[C:13]([O:23][CH3:24])[CH:12]=3)/[C:4]2=[O:25])[CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 10313191(6-Chloropyridin-2-yl)methanamineHCID 66960126HCID 66960126, compound

Product 1

HCID 11524651HCID 11524651, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of (E)-5-chloro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl]benzylidene)valeric acid ethyl ester (200 mg) obtained in Example 417 and 2-(aminomethyl)-6-chloropyridine (CA 188637-75-4) hydrochloride (100 mg) in ethanol (3 mL) and DMF (3 mL), anhydrous potassium carbonate (100 mg) was added and the reaction mixture was agitated at 100° C. for 8 hours. After the reaction mixture was allowed to be cooled to room temperature, the reaction mixture was poured into iced water and the reaction solution was extracted with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, and concentrated under reduced pressure after dried over anhydrous magnesium sulfate. Ethanol (10 mL) and sodium hydroxide (1.0 g) aqueous solution (5 mL) were added to the residue, and the reaction solution was agitated at room temperature for 1 hour. The reaction solution was added to iced water and the reaction solution was extracted with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, and it concentrated under reduced pressure after dried over anhydrous magnesium sulfate. 23 mg of the title compound was obtained by the residue was purified by silica gel chromatography (elution solvent:heptane-ethyl acetate system).

Workup

  1. additionwas added
  2. temperatureto be cooled to room temperature
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with a saturated sodium chloride solution
  5. concentrationconcentrated under reduced pressure
  6. dry with materialafter dried over anhydrous magnesium sulfate
  7. additionEthanol (10 mL) and sodium hydroxide (1.0 g) aqueous solution (5 mL) were added to the residue
  8. stirringthe reaction solution was agitated at room temperature for 1 hour
  9. additionThe reaction solution was added to iced water
  10. extractionthe reaction solution was extracted with ethyl acetate
  11. washThe obtained organic layer was washed with a saturated sodium chloride solution, and it
  12. concentrationconcentrated under reduced pressure
  13. dry with materialafter dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-20efb413e4e44c1c9d5ba65654425cde
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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