1,1'-Carbonyldiimidazole → 7-Chloro-3-(aminocarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione

HRID 428423Notes

Reaction equation

HRID 428423 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[C:7]3[C:14]([C:15](O)=[O:16])=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.C(N1C=CN=C1)([N:23]1C=CN=C1)=O.C([O-])(=O)C.[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[C:7]3[C:14]([C:15]([NH2:23])=[O:16])=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 517165Ammonium AcetateHCID 178524941HCID 178524941, compound2×

Product 1

HCID 183588967-Chloro-3-(aminocarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dioneYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 7-chloro-3-(carboxy)pyrazolo[3,4-c][1]-benzazepine-4,10-(1H,9H)-dione (1 g, 3.44 mmol) (compound of Example 9) and 1,1′-carbonyldiimidazole (0.64 mg, 3.95 mmol) in N,N-dimethylformamide (25 mL) was stirred for 64.5 hours. In one portion, ammonium acetate (0.796 mg, 10.33 mmol) was added, followed by additional N,N-dimethylformamide (15 mL). The solution was stirred for 3.75 hours at room temperature and concentrated in vacuo for 45 minutes. The residue was washed with water (63×20 mL). The insoluble material was filtered and dried to give the title compound (967 mg, 97% yield, m.p. 224-225° C.).

Workup

  1. concentrationconcentrated in vacuo for 45 minutes
  2. washThe residue was washed with water (63×20 mL)
  3. filtrationThe insoluble material was filtered
  4. customdried

Sources & evidence

ORD record
ord-b0ad15c6e98e41a0af1ac7d818381eab
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

Loading…