Hydroxylamine → HCID 178526082, compound

HRID 428422Notes

Reaction equation

HRID 428422 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.[CH2:34]([NH:41]O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C.NO>CN(C)C=O.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:41][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:16])=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Participants

8

Reactant 5

HCID 787HydroxylamineHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 11332622N-benzylhydroxylamine hydrochlorideHCID 178524941HCID 178524941, compound2×

Product 1

HCID 178526082HCID 178526082, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 7-chloro-3-(carboxy)pyrazolo[3,4-c][1]-benzazepine-4,10(1H,9H)-dione (100 mg, 0.344 mmol) (compound of Example 9) and 1,1′-carbonyldiimidazole (83.5 mg, 0.515 mmol) in N,N-dimethylformamide (1.4 mL) was stirred for 1 hour. In a separate flask was placed N-benzylhydroxylamine hydrochloride (82.2 mg, 0.515 mmol), triethylamine (71.7 μL, 0.515 mmol), and N,N-dimethylformamide (2 mL). This solution was stirred for 20 minutes. The hydroxylamine solution was added to the acylimidazole solution and the resulting solution was stirred for 1 hour at 70° C. The solution was cooled to room temperature and water (10 mL) was added. The insoluble material was filtered and dried to give the title compound (110 mg, 81% yield, m.p. 169-179° C. dec).

Workup

  1. customIn a separate flask was placed
  2. stirringthe resulting solution was stirred for 1 hour at 70° C
  3. filtrationThe insoluble material was filtered
  4. customdried

Sources & evidence

ORD record
ord-40bf6e5964764bb09fb5b0b6206224f4
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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