Acetic Acid → 4-[5-(1H-indazol-6-yl)-1H-imidazol-2-yl]-2-nitrophenylamine

HRID 388979Notes

Reaction equation

HRID 388979 reaction equation
CC[N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])[CH3:5].BrCC(C1[CH:22]=[C:21]2[C:17]([CH:18]=[N:19][NH:20]2)=[CH:16][CH:15]=1)=O.[NH2:23][C:24]1[CH:32]=[CH:31]C(C(O)=O)=[CH:26][C:25]=1[N+:33]([O-:35])=[O:34].CC(O)=O.C[N:41](C=O)C>O>[NH:20]1[C:21]2[C:17](=[CH:16][CH:15]=[C:6]([C:4]3[NH:3][C:7]([C:9]4[CH:31]=[CH:32][C:24]([NH2:23])=[C:25]([N+:33]([O-:35])=[O:34])[CH:26]=4)=[N:41][CH:5]=3)[CH:22]=2)[CH:18]=[N:19]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 81531DiisopropylethylamineHCID 866152232-bromo-1-(1H-indazol-6-yl)ethan-1-one

Product 1

HCID 684463374-[5-(1H-indazol-6-yl)-1H-imidazol-2-yl]-2-nitrophenylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DIEA (0.7 mL, 3.6 mmol) was added to a solution of 2-bromo-1-(1H-indazol-6-yl)ethanone (3 mmol) and 4-amino-3-nitrobenzoic acid (0.643 g, 3.5 mmol) in DMF (10 mL) and the solution was stirred at room temperature for 2 h. NH4OAc (5 g, 65 mmol) was added to the solution, followed by HOAc (10 mL) and the mixture was stirred at 140° C. for 2 h. The mixture was cooled to room temperature and poured into H2O (30 mL). The precipitate was collected by filtration, washed with H2O (10 mL) and dried under reduced pressure to afford 4-[5-(1H-indazol-6-yl)-1H-imidazol-2-yl]-2-nitrophenylamine (0.56 g).

Workup

  1. stirringthe mixture was stirred at 140° C. for 2 h
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with H2O (10 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-3555a85afa3447a5ad64a01d82625d58
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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