Water → 7-Chloro-3-[[(tert-butylamino)oxy]carbonyl]pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione

HRID 428419Notes

Reaction equation

HRID 428419 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.Cl.[C:34]([NH:38]O)([CH3:37])([CH3:36])[CH3:35].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][NH:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[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 682631,1'-CarbonyldiimidazoleHCID 2777896N-tert-butylhydroxylamine hydrochlorideHCID 178524941HCID 178524941, compound2×

Product 1

HCID 1784499477-Chloro-3-[[(tert-butylamino)oxy]carbonyl]pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dioneYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-chloro-3-(carboxy)pyrazolo[3,4-c][1]-benzazepine-4,10(1H,9H)-dione (400 mg, 1.37 mmol) (compound of Example 9) and 1,1′-carbonyldiimidazole (334 mg, 2.06 mmol) in N,N-dimethylformamide (16 mL) was stirred for 1 hour. In one portion, N-tert-butylhydroxylamine hydrochloride (516 mg, 4.11 mmol) was added and the solution was stirred for 17 hours at room temperature. To the resulting solution was added water (20 mL). The insoluble material was filtered and washed with hot methanol (3×20 mL) to give the title compound (300 mg, 61% yield, m.p. 258° C.).

Workup

  1. filtrationThe insoluble material was filtered
  2. washwashed with hot methanol (3×20 mL)

Sources & evidence

ORD record
ord-51e08f90a2bb441ea101b0be1eafcb1e
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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