Benzaldehyde → HCID 87274243, compound

HRID 1615892Notes

Reaction equation

HRID 1615892 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:7]=[C:8]([C:11]2[N:12]=[C:13]([NH:22][C:23](=[O:32])[C:24]3[CH:29]=[CH:28][N:27]=[C:26]([O:30][CH3:31])[CH:25]=3)[S:14][C:15]=2[N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[S:9][CH:10]=1.[CH:33](=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].[OH-].[Na+]>ClCCCl.C(O)(=O)C>[ClH:5].[CH2:33]([N:19]1[CH2:20][CH2:21][N:16]([C:15]2[S:14][C:13]([NH:22][C:23](=[O:32])[C:24]3[CH:29]=[CH:28][N:27]=[C:26]([O:30][CH3:31])[CH:25]=3)=[N:12][C:11]=2[C:8]2[S:9][CH:10]=[C:6]([Cl:5])[CH:7]=2)[CH2:17][CH2:18]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23030578HCID 23030578, compound

Product 1

HCID 87274243HCID 87274243, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

231 mg of the compound of Example 10 and 80 μl of benzaldehyde were dissolved in 9 ml of 1,2-dichloroethane-9 ml of acetic acid, 210 mg of sodium triacetoxyborohydride was added thereto at 0° C., and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 30 minutes. The reaction solution was alkalinized with saturated aqueous NaHCO3 and 1M aqueous NaOH, and extracted with chloroform. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. Then, to the obtained residue, 5 ml of acetic acid, a total of 160 μl of benzaldehyde, and a total of 404 mg of sodium triacetoxyborohydride were added, and the mixture was stirred at 50° C. for 4 hours. The solvent was evaporated under reduced pressure, saturated aqueous NaHCO3 was added to the obtained residue, and insoluble matter was collected by filtration. Chloroform was added thereto to dissolve it, and the solution was mixed with saturated aqueous NaHCO3 and extracted with chloroform. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-EtOAc=4:1) and the obtained compound was dissolved in EtOAc, and then a 0.5 M HCl.EtOAc solution was added thereto, and the thus-produced precipitate was collected by filtration to obtain 64 mg of N-[5-(4-benzylpiperazin-1-yl)-4-(4-chlorothiophen-2-yl)thiazol-2-yl]-2-methoxyisonicotinamide hydrochloride.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. additionThen, to the obtained residue, 5 ml of acetic acid, a total of 160 μl of benzaldehyde, and a total of 404 mg of sodium triacetoxyborohydride were added
  6. stirringthe mixture was stirred at 50° C. for 4 hours
  7. customThe solvent was evaporated under reduced pressure, saturated aqueous NaHCO3
  8. additionwas added to the obtained residue, and insoluble matter
  9. filtrationwas collected by filtration
  10. additionChloroform was added
  11. dissolutionto dissolve it
  12. additionthe solution was mixed with saturated aqueous NaHCO3
  13. extractionextracted with chloroform
  14. dry with materialThe organic layer was dried over MgSO4
  15. customthe solvent was evaporated under reduced pressure
  16. customThe obtained residue was purified by silica gel column chromatography (hexane-EtOAc=4:1)
  17. dissolutionthe obtained compound was dissolved in EtOAc
  18. additionEtOAc solution was added
  19. filtrationthe thus-produced precipitate was collected by filtration

Sources & evidence

ORD record
ord-23609cbbfe294b5f83b42293f8bf2e38
Source dataset
uspto-grants-2014_07
Patent number
US08765764B2

Reaction notes

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