1,1'-Carbonyldiimidazole → 3,6-Dichloro-pyridazine-4-carboxylic acid (2-amino-3-carbamoylphenyl)-amide

HRID 1670399Notes

Reaction equation

HRID 1670399 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8](O)=[O:9].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:24][C:25]1[C:33]([NH2:34])=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([NH2:29])=[O:28]>CN(C=O)C.N1C=CC=CC=1>[NH2:24][C:25]1[C:26]([C:27](=[O:28])[NH2:29])=[CH:30][CH:31]=[CH:32][C:33]=1[NH:34][C:8]([C:7]1[CH:6]=[C:5]([Cl:11])[N:4]=[N:3][C:2]=1[Cl:1])=[O:9]

Participants

6

Reactant 3

HCID 682631,1'-Carbonyldiimidazole2×HCID 4338043,6-Dichloropyridazine-4-carboxylic acidHCID 104870292,3-Diaminobenzamide

Product 1

HCID 580241553,6-Dichloro-pyridazine-4-carboxylic acid (2-amino-3-carbamoylphenyl)-amide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3,6-Dichloropyridazine-4-carboxylic acid (1.15 g, 5.96 mmol) and 1,1′-carbonyldiimidazole (CDI (0.97 g) in DMF (25 ml) were stirred at room temperature for 2 h. A solution of 2,3-diaminobenzamide (1.30 g, 5.96 mmol) in pyridine (25 ml) was added and the solution heated at 50° C. for 4 h. The cooled solution was concentrated and partitioned between ethyl acetate (EtOAc) and water, the organic layer separated, dried, filtered and concentrated to give the product.

Workup

  1. concentrationThe cooled solution was concentrated
  2. custompartitioned between ethyl acetate (EtOAc) and water
  3. customthe organic layer separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the product

Sources & evidence

ORD record
ord-a98bd9e3384a43a8bd00cfc5e866829b
Source dataset
uspto-grants-2011_08
Patent number
US07994160B2

Reaction notes

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