Triphenylphosphine → HCID 67461046, compound

HRID 1620010Notes

Reaction equation

HRID 1620010 reaction equation
[CH2:1]([CH:3]1[C:8]([C:9]2[CH:24]=[CH:23][C:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=4)[O:15][C:11]=3[CH:10]=2)=[N:7][NH:6][C:5](=[O:25])[CH2:4]1)[CH3:2].[CH2:26]([N:28]([CH:32]([CH3:34])[CH3:33])[CH2:29][CH2:30]O)[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>CC(=O)OCC.C1COCC1>[CH2:1]([CH:3]1[C:8]([C:9]2[CH:24]=[CH:23][C:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:27][CH2:26][N:28]([CH2:29][CH3:30])[CH:32]([CH3:34])[CH3:33])=[CH:18][CH:17]=4)[O:15][C:11]=3[CH:10]=2)=[N:7][NH:6][C:5](=[O:25])[CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 22218487HCID 22218487, compoundHCID 1360889275-ethyl-6-[2-(4-hydroxy-phenyl)-benzoxazol-6-yl]-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 67461046HCID 67461046, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

40 mg (119 μmol) 5-ethyl-6-[2-(4-hydroxy-phenyl)-benzoxazol-6-yl]-4,5-dihydro-2H-pyridazin-3-one, 31 mg (238 μmol) 2-(ethyl-isopropyl-amino)-ethanol, 66 mg (251 μmol) triphenylphosphine and 5 ml THF are placed under protective gas. At 0° C., 58 mg (251 μmol) of DBAD are added and then the mixture is stirred overnight at RT. Then it is diluted with EA and extracted with 10% sodium carbonate solution. The organic phase is stirred with 15 mL of 4N HCl for 5 min and then extracted twice with diethyl ether. The acid H2O phase is made basic with sodium carbonate solution and extracted 3 times with DCM. The organic phase is washed with saturated saline solution and then the solv. is eliminated i.V. The residue is recrystallised with cyclohexane/EA.

Workup

  1. extractionextracted with 10% sodium carbonate solution
  2. stirringThe organic phase is stirred with 15 mL of 4N HCl for 5 min
  3. extractionextracted twice with diethyl ether
  4. extractionextracted 3 times with DCM
  5. washThe organic phase is washed with saturated saline solution
  6. customThe residue is recrystallised with cyclohexane/EA

Sources & evidence

ORD record
ord-7ef1c7c56ccd4fbb8ce287085f3b655b
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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