3,6-Dichloro-pyridazine-4-carboxylic acid (2-amino-3-carbamoylphenyl)-amide → 2-Chloro-11-oxo-10,11-dihydro-5H-3,4,5,10-tetraaza-dibenzo[a,d]cycloheptene-6-carboxylic acid amide

HRID 1670400Notes

Reaction equation

HRID 1670400 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:10])[NH2:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[CH:19]=[C:18]([Cl:20])[N:17]=[N:16][C:15]=1Cl)=[O:13]>C(O)(=O)C>[Cl:20][C:18]1[N:17]=[N:16][C:15]2[NH:1][C:2]3[C:7]([C:8]([NH2:9])=[O:10])=[CH:6][CH:5]=[CH:4][C:3]=3[NH:11][C:12](=[O:13])[C:14]=2[CH:19]=1

Participants

3

Reactant 1

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

Product 1

HCID 159862732-Chloro-11-oxo-10,11-dihydro-5H-3,4,5,10-tetraaza-dibenzo[a,d]cycloheptene-6-carboxylic acid amideYield 51.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3,6-Dichloro-pyridazine-4-carboxylic acid (2-amino-3-carbamoyl-phenyl)-amide (500 mg, 1.53 mmol) in acetic acid (AcOH) (25 ml) was heated at 100° C. for 1 h. The cooled solution was concentrated and partitioned between EtOAc and saturated Na—HCO3, the organic layer separated, dried, filtered and concentrated to give the product as a brown solid (227 mg, 51%).

Workup

  1. concentrationThe cooled solution was concentrated
  2. custompartitioned between EtOAc and saturated Na—HCO3
  3. customthe organic layer separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e1de213dc2b24b32bb7581b1e9ffd72f
Source dataset
uspto-grants-2011_08
Patent number
US07994160B2

Reaction notes

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