Water → HCID 178524292, compound

HRID 428424Notes

Reaction equation

HRID 428424 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]([OH:17])=[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)(N1C=CN=C1)=O.[C:33]1(O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>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]([O:17][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:16])=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 682631,1'-CarbonyldiimidazoleHCID 178524941HCID 178524941, compound2×

Product 1

HCID 178524292HCID 178524292, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 7-chloro-3-(carboxy)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (500 mg, 1.72 mmol) (compound of Example 9) and 1,1′-carbonyldiimidazole (418 mg, 2.58 mmol) in N,N-dimethylformamide (7 mL) was stirred for 16.75 hours. In one portion, phenol (486 mg, 5.16 mmol) was added and the solution was stirred for 24 hours at 70° C. To the resulting solution was added water (30 mL), giving a precipitate which was separated by filtration. This crude product was purified by chromatography eluting with chloroform: 2-propanol (98:2-90:10) to give the title compound (330 mg, 53% yield, m.p. 265° C.).

Workup

  1. customgiving a precipitate which
  2. customwas separated by filtration
  3. customThis crude product was purified by chromatography
  4. washeluting with chloroform: 2-propanol (98:2-90:10)

Sources & evidence

ORD record
ord-b268d3eaa03d44a9b80a181ee84afa3b
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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