Sodium borohydride → 5-ethyl-6-{2-[4-(2-hydroxy-propoxy)-phenyl]-benzoxazol-6-yl}-4,5-dihydro-2H-pyridazin-3-one

HRID 1619953Notes

Reaction equation

HRID 1619953 reaction equation
[CH2:1]([CH:3]1[C:8]([C:9]2[CH:28]=[CH:27][C:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24](=[O:26])[CH3:25])=[CH:18][CH:17]=4)[O:15][C:11]=3[CH:10]=2)=[N:7][NH:6][C:5](=[O:29])[CH2:4]1)[CH3:2].[BH4-].[Na+]>CCO>[CH2:1]([CH:3]1[C:8]([C:9]2[CH:28]=[CH:27][C:12]3[N:13]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH:24]([OH:26])[CH3:25])=[CH:20][CH:21]=4)[O:15][C:11]=3[CH:10]=2)=[N:7][NH:6][C:5](=[O:29])[CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67467398HCID 67467398, compound

Product 1

HCID 674668885-ethyl-6-{2-[4-(2-hydroxy-propoxy)-phenyl]-benzoxazol-6-yl}-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

27 mg (69 μmol) 5-ethyl-6-{2-[4-(2-oxo-propoxy)-phenyl]-benzoxazol-6-yl}-4,5-dihydro-2H pyridazin-3-one are placed in 5 mL EtOH, 5.5 mg (145 μmol) sodium borohydride are added with cooling and the mixture is stirred for 3 h at RT. The reaction mixture is added to 50 mL ice water and extracted with DCM. The org. phase is washed with sat. saline solution and then the solv. is totally eliminated i.V. The residue is crystallised from cyclohexane/EA.

Workup

  1. temperaturewith cooling
  2. extractionextracted with DCM
  3. washphase is washed with sat. saline solution
  4. customThe residue is crystallised from cyclohexane/EA

Sources & evidence

ORD record
ord-d004e25c1b3a4d4eaf1daae77832d5fb
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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