Water → 6-Chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid amide

HRID 500519Notes

Reaction equation

HRID 500519 reaction equation
[Cl:1][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)[CH:3]=1.C(N1C=CN=C1)([N:22]1C=CN=C1)=O.C([O-])(=O)C.[NH4+].O>CN(C)C=O>[Cl:1][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]([NH2:22])=[O:19])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 517165Ammonium AcetateHCID 248220276-Chloro-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxylic acid

Product 1

HCID 177472136-Chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxylic acid (144 mg, 0.37 mmol.) and 1,1′-carbonylbis(1H-imidazole) (119 mg, 0.73 mmol) were suspended in N,N-dimethylformamide (1.00 ml). The mixture was stirred over night (12 hr). Solid ammonium acetate (31 mg, 0.40 mmol) then added. The reaction was stirred for another 5 h. Water (0.5 mL) was then added into the mixture. The desired product was precipitated and was collected by vacuum filtration. LC/MS [7.39 min; 393 (M+1)].

Workup

  1. stirringThe reaction was stirred for another 5 h
  2. customThe desired product was precipitated
  3. filtrationwas collected by vacuum filtration
  4. customLC/MS [7.39 min; 393 (M+1)]

Sources & evidence

ORD record
ord-358c691e7f304162b7d04dbcbb334e6c
Source dataset
uspto-grants-2010_08
Patent number
US07772233B2

Reaction notes

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