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

HRID 500520Notes

Reaction equation

HRID 500520 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:20](N1C=CN=C1)([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=O.N1C[CH2:36][O:35][CH2:34]C1.O>CN(C)C=O>[N:22]1([CH2:26][CH2:25][NH:24][C:17]([C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=2[NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[O:19])[CH2:23][CH2:36][O:35][CH2:34][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 248220276-Chloro-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxylic acid

Product 1

HCID 248220296-Chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid (2-morpholin-4-yl-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-chloro-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxylic acid (32 mg, 0.08 mmol.) and 1,1′-carbonylbis(1H-imidazole) (15.4 mg, 0.09 mmol) were suspended in N,N-dimethylformamide (0.6 ml). The mixture was stirred over night (12 hr). Morpholine (21.2 mg, 0.16 mmol) was 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 [4.69 min; 506 (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 [4.69 min; 506 (M+1)]

Sources & evidence

ORD record
ord-f339d310e73a466ca8a0d06e185d19ad
Source dataset
uspto-grants-2010_08
Patent number
US07772233B2

Reaction notes

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