HCID 68443943, compound → HCID 68445902, compound

HRID 1163417Notes

Reaction equation

HRID 1163417 reaction equation
[NH2:1][C:2]1[C:19]([N+:20]([O-])=O)=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[O:7])=[C:4]([Cl:23])[CH:3]=1>C(O)C.CC(O)=O.[Fe]>[NH2:1][C:2]1[C:19]([NH2:20])=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[O:7])=[C:4]([Cl:23])[CH:3]=1

Participants

5

Reactant 1

HCID 68443943HCID 68443943, compound

Product 1

HCID 68445902HCID 68445902, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 4-amino-2-chloro-N-(1H-indazol-6-yl)-5-nitrobenzamide (2 mmol; see Example 154) in ethanol (5 mL) and AcOH (1 mL) was added with iron powder (10 mmol). The reaction mixture was then heated to reflux for 6 h. The contents were cooled to RT, filtered through Celite pad, and the pad washed with ethanol. The filtrates were combined and concentrated in vacuo. The residue obtained was purified on a silica gel column chromatography using MeOH/DCM as eluent to afford 4,5-diamino-2-chloro-N-(1H-indazol-6-yl)benzamide.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 6 h
  3. filtrationfiltered through Celite pad
  4. washthe pad washed with ethanol
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas purified on a silica gel column chromatography

Sources & evidence

ORD record
ord-1721bce0f9cd49e298ff5c1748775ebb
Source dataset
uspto-grants-2010_10
Patent number
US07820821B2

Reaction notes

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