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

HRID 2404222Notes

Reaction equation

HRID 2404222 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-bd1419ac62af4b2d861b6089687a54f7
Source dataset
uspto-grants-2014_08
Patent number
US08802703B2

Reaction notes

Loading…