1H-Indazol-6-amine → 2-[(4-t-Butylbenzoyl)amino]-N-(6-indazolyl)-5-nitrobenzamide

HRID 2301832Notes

Reaction equation

HRID 2301832 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[O:10][C:9](=[O:23])[C:8]=2[CH:24]=1)([O-:3])=[O:2].[NH2:25][C:26]1[CH:34]=[C:33]2[C:29]([CH:30]=[N:31][NH:32]2)=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:11]([NH:12][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:24][C:8]=2[C:9]([NH:25][C:26]2[CH:34]=[C:33]3[C:29]([CH:30]=[N:31][NH:32]3)=[CH:28][CH:27]=2)=[O:23])=[O:10])=[CH:14][CH:15]=1)([CH3:20])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 814231H-Indazol-6-amineHCID 3855992-(4-Tert-butylphenyl)-6-nitro-3,1-benzoxazin-4-one

Product 1

HCID 183731892-[(4-t-Butylbenzoyl)amino]-N-(6-indazolyl)-5-nitrobenzamideYield 42.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirring solution of 6-nitro-2-[4-t-butylphenyl]-4H-3,1-benzoxazin-4-one (1.5 g, 4.62 mmol) in toluene (25 mL) was added 6-aminoindazole (560 mg, 4.2 mmol) and the solution was heated to reflux. After about 24 h, the solution was cooled, filtered and the solid was washed with diethyl ether. The product was then chromatographed over silica gel, eluting with 25% ethyl acetate/hexanes. The product containing fractions were combined and concentrated in vacuo to give 810 mg (42%) of pale yellow solid.

Workup

  1. temperaturethe solution was heated to reflux
  2. temperaturethe solution was cooled
  3. filtrationfiltered
  4. washthe solid was washed with diethyl ether
  5. customThe product was then chromatographed over silica gel
  6. washeluting with 25% ethyl acetate/hexanes
  7. additionThe product containing fractions
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18c6f70c36e346d5827d0dfae8f62296
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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