Dimethylformamide → HCID 67465409, compound

HRID 1620011Notes

Reaction equation

HRID 1620011 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].Br[CH2:27][CH:28]([O:31][CH3:32])[O:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CC(=O)OCC>[CH3:30][O:29][CH:28]([O:31][CH3:32])[CH2:27][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[O:15][C:11]3[CH:10]=[C:9]([C:8]4[CH:3]([CH2:1][CH3:2])[CH2:4][C:5](=[O:25])[NH:6][N:7]=4)[CH:24]=[CH:23][C:12]=3[N:13]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 1360889275-ethyl-6-[2-(4-hydroxy-phenyl)-benzoxazol-6-yl]-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 67465409HCID 67465409, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

100 mg (298 μmol) 5-ethyl-6-[2-(4-hydroxy-phenyl)-benzoxazol-6-yl]-4,5-dihydro-2H-pyridazin-3-one, 38.5 μL (316 μmol) 2-bromo-1,1-dimethoxy-ethane, 125 mg (904 μmol) potassium carbonate and 3 ml DMF are stirred for 6 h at 150° C. and then at RT over the weekend. Then the mixture is diluted with EA, and extracted with 10% sodium carbonate solution and then with sat. saline solution. The solv. of the org. phase is eliminated i.V. The residue is purified on silica gel (eluant: DCM/methanol) the solv. of the corresponding fractions is eliminated i.V. and the residue is recrystallised with EA/cyclohexane.

Workup

  1. customat RT
  2. extractionextracted with 10% sodium carbonate solution
  3. customThe residue is purified on silica gel (eluant: DCM/methanol) the solv
  4. customand the residue is recrystallised with EA/cyclohexane

Sources & evidence

ORD record
ord-accd9616a78f4a99ac3d0ecd2446da49
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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