Citric Acid → HCID 54591572, compound

HRID 1619973Notes

Reaction equation

HRID 1619973 reaction equation
[CH3:1][C:2]1[C:3]([C:9]2[CH:27]=[CH:26][C:12]3[N:13]=[C:14]([C:16]4[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=4)[O:15][C:11]=3[CH:10]=2)=[N:4][NH:5][C:6](=[O:8])[CH:7]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[CH3:1][C:2]1[C:3]([C:9]2[CH:27]=[CH:26][C:12]3[N:13]=[C:14]([C:16]4[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=4)[O:15][C:11]=3[CH:10]=2)=[N:4][NH:5][C:6](=[O:8])[CH:7]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 67466265HCID 67466265, compound

Product 1

HCID 54591572HCID 54591572, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

25 mg (69 μmol) methyl 4-[6-(4-methyl-6-oxo-1,6-dihydro-pyridazin-3-yl)-benzoxazol-2-yl]-benzoate is placed in 4 mL DMSO, 350 μL (1 mmol/mL; 346 μmol) sodium hydroxide solution are added and the mixture is stirred overnight at RT. The reaction mixture is adjusted to pH 4 with 10% citric acid and extracted with H2O and DCM. Then the solv. of the organic phase is eliminated i.V. and the residue is separated by HPLC-MS. (xTerra, ACN/H2O+TFA)

Workup

  1. extractionextracted with H2O and DCM
  2. customand the residue is separated by HPLC-MS

Sources & evidence

ORD record
ord-ec023d17cf0a48d2a91c52e0f806cfa1
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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