2-Methoxyethanol → HCID 68209375, compound

HRID 1620009Notes

Reaction equation

HRID 1620009 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].[CH3:26][O:27][CH2:28][CH2:29]O.C1(P(C2C=CC=CC=2)C2C=CC=CN=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][CH2:29][CH2:28][O:27][CH3:26])=[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 80192-MethoxyethanolHCID 6218932-PyridyldiphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 136088927HCID 136088927, compound

Product 1

HCID 68209375HCID 68209375, 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, 19 μL (241 μmol) 2-methoxyethanol, 66 mg (251 μmol) diphenyl-2-pyridylphosphine and 10 ml THF are placed under protective gas. At 0° C. 58 mg (252 μmol) 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 20 mL of 4N HCl for 5 min and then extracted. The organic phase is washed with saturated saline solution and then the solv. is eliminated i.V. The residue is purified on silica gel. (Eluant: DCM/MeOH/ammonia) The solv. of the corresponding fractions is eliminated i.V. and the residue is crystallised with cyclohexane/EA.

Workup

  1. customAt 0° C
  2. extractionextracted with 10% sodium carbonate solution
  3. stirringThe organic phase is stirred with 20 mL of 4N HCl for 5 min
  4. extractionextracted
  5. washThe organic phase is washed with saturated saline solution
  6. customThe residue is purified on silica gel
  7. customand the residue is crystallised with cyclohexane/EA

Sources & evidence

ORD record
ord-db4ecefdbb264fd4a8e0a3cf19be5029
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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