N-methyl-2-pyrrolidone → 8-amino-1-{4-[(aminothio)peroxy]phenyl}-1H-benzo[g]indazole-3-carboxamide

HRID 22980

Reaction equation

HRID 22980 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]2[CH2:6][CH2:7][C:8]3[C:9]([C:23]([NH2:25])=[O:24])=[N:10][N:11]([C:13]4[CH:18]=[CH:17][C:16]([O:19][O:20][S:21][NH2:22])=[CH:15][CH:14]=4)[C:12]=3[C:4]=2[CH:3]=1.CN1C(=O)CCC1>C1(C(C)C)C=CC=CC=1.[Pd]>[NH2:1][C:2]1[CH:27]=[CH:26][C:5]2=[CH:6][CH:7]=[C:8]3[C:12]([N:11]([C:13]4[CH:18]=[CH:17][C:16]([O:19][O:20][S:21][NH2:22])=[CH:15][CH:14]=4)[N:10]=[C:9]3[C:23]([NH2:25])=[O:24])=[C:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 222915508-amino-1-{4-[(aminothio)peroxy]phenyl}-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

Product 1

HCID 225925248-amino-1-{4-[(aminothio)peroxy]phenyl}-1H-benzo[g]indazole-3-carboxamideYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7406CumeneSolvent

Procedure

The product of Example 4b (1 g) and 5% Pd/C (300 mg) suspended in cumene (50 mL) and NMP (5 mL) was heated at reflux for 16 h. The mixture was then filtered and concentrated. The residue was diluted with methanol (10 mL) and added to water, after 1 h the resulting precipitate was collected by filtration and dried to yield the title compound (0.9 g).

Workup

  1. temperatureat reflux for 16 h
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated
  4. additionThe residue was diluted with methanol (10 mL)
  5. additionadded to water, after 1 h the resulting precipitate
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-8fce33b15a5c4c0e9f5294a5695d02da
Source dataset
uspto-grants-2005_02
Patent number
US06849653B2

Linked notes

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