Pyridine → 8-(Acetylamino)-1-{4-[(aminothio)peroxy]phenyl}-4,5-dihydro-1h-benzo[g]indazole-3-carboxamide

HRID 22981Notes

Reaction equation

HRID 22981 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.[C:28](OC(=O)C)(=[O:30])[CH3:29].N1C=CC=CC=1>CN(C=O)C.O>[C:28]([NH: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:14]=[CH:15][C:16]([O:19][O:20][S:21][NH2:22])=[CH:17][CH:18]=4)[C:12]=3[C:4]=2[CH:3]=1)(=[O:30])[CH3:29]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 222915508-amino-1-{4-[(aminothio)peroxy]phenyl}-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

Product 1

HCID 222918058-(Acetylamino)-1-{4-[(aminothio)peroxy]phenyl}-4,5-dihydro-1h-benzo[g]indazole-3-carboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To the material of Example 4b (1.0 g, 0.0026 mol) in DMF (15 mL) was added dropwise a mixture of acetic anhydride (0.283 mL, 0.003 mol) and pyridine (0.243 mL, 0.003 mol) in DMF (5 mL). Contents were stirred overnight, diluted with water (75 mL), and filtered to give the desired as a white solid, 1.0 g (90% yield). FABHRMS m/z 426.1235 (M+H, C20H20N5O4S requires 426.1236). 1H NMR (DMSO-d6/300 MHz) 9.80 (s, 1H); 8.00 (d, 2H); 7.75 (d, 2H); 7.60 (s, 1H); 7.48 (s, 2H); 7.39 (s, 1H); 7.30 (d, 1H); 7.15 (s, 1H); 2.90 (s, 4H); 1.92 (s, 3H). Anal. Calcd for C20H19N5O4S (1H2O): C, 54.17; H, 4.77; N, 15.79. Found: C, 54.20; H, 4.97; N, 15.77.

Workup

  1. filtrationfiltered
  2. customto give the

Sources & evidence

ORD record
ord-c6fb776b7fb54d0488b78a408fa548fd
Source dataset
uspto-grants-2005_02
Patent number
US06849653B2

Reaction notes

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