Sodium Methoxide → 3-(2-Fluoro-4-iodo-phenylamino)-6-methoxy-pyridazine-4-carboxylic acid

HRID 500516Notes

Reaction equation

HRID 500516 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[C:4]([C:17]([OH:19])=[O:18])[CH:3]=1.[CH3:20][O-:21].[Na+]>CN(C=O)C.CCOCC>[F:16][C:10]1[CH:11]=[C:12]([I:15])[CH:13]=[CH:14][C:9]=1[NH:8][C:5]1[N:6]=[N:7][C:2]([O:21][CH3:20])=[CH:3][C:4]=1[C:17]([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 248220276-Chloro-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxylic acid

Product 1

HCID 248219663-(2-Fluoro-4-iodo-phenylamino)-6-methoxy-pyridazine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To solid 6-chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid (34 mg, 0.09 mmol) in DMF was added NaOMe (0.43 mmol, 0.5 M in MeOH). The mixture was heated at 135° C. for 3 h. The mixture was diluted with ether and extracted with NaOH (1N). The aqueous layer was acidified by concentrated HCl. The desired product was precipitated and was collected by vacuum filtration. LC/MS [8.08 min; 390 (M+1)].

Workup

  1. extractionextracted with NaOH (1N)
  2. customThe desired product was precipitated
  3. filtrationwas collected by vacuum filtration
  4. customLC/MS [8.08 min; 390 (M+1)]

Sources & evidence

ORD record
ord-85d146ab88da45308c0ff7b576afc8a6
Source dataset
uspto-grants-2010_08
Patent number
US07772233B2

Reaction notes

Loading…