1-Bromo-2,4-dimethyl-5-nitrobenzene → 1-(2,2-Diethoxyethyl)-N-(2,4-dimethyl-5-nitrophenyl)-3-(pyridazin-3-yl)-1H-pyrazole-5-amine

HRID 1055695Notes

Reaction equation

HRID 1055695 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[CH2:5][N:6]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]2[N:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:7]1)[CH3:2].Br[C:22]1[C:23]([CH3:32])=[CH:24][C:25]([CH3:31])=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=1>>[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[CH2:5][N:6]1[C:10]([NH:11][C:22]2[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([CH3:31])=[CH:24][C:23]=2[CH3:32])=[CH:9][C:8]([C:12]2[N:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:7]1)[CH3:2]

Participants

3

Reactant 2

HCID 124743261-Bromo-2,4-dimethyl-5-nitrobenzeneHCID 896999951-(2,2-Diethoxyethyl)-3-(pyridazin-3-yl)-1H-pyrazole-5-amine

Product 1

HCID 896998211-(2,2-Diethoxyethyl)-N-(2,4-dimethyl-5-nitrophenyl)-3-(pyridazin-3-yl)-1H-pyrazole-5-amine

Procedure

Analogously to Example 13A/Step 1, 1.09 g (3.93 mmol) of the compound of Example 80A and 996 mg (4.33 mmol) of 5-bromo-2,4-dimethylnitrobenzene gave, after 3 h of heating under reflux, a crude product which was purified by chromatography on a Biotage system (100 g Snap column; mobile phase gradient ethyl acetate/0-8% methanol). This gave 1.38 g (77% of theory) of the title compound.

Workup

  1. customgave, after 3 h
  2. temperatureof heating
  3. temperatureunder reflux
  4. customa crude product which was purified by chromatography on a Biotage system (100 g Snap column; mobile phase gradient ethyl acetate/0-8% methanol)

Sources & evidence

ORD record
ord-3eab51675e1c4bdfa70b45076fc9bf5e
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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