Dimethylformamide → HCID 178434097, compound

HRID 2095192Notes

Reaction equation

HRID 2095192 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[NH2:10][C:11]1[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=1.C[N:18](C=O)C>O>[F:1][C:2]1[CH:3]=[C:4]([NH:5][N:18]=[C:15]2[C:14]([CH3:16])=[N:13][N:12]=[C:11]2[NH2:10])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 774693,4-DifluoroanilineHCID 931461H-Pyrazol-3-amine, 5-methyl-

Product 1

HCID 178434097HCID 178434097, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[(3,4-difluorophenyl)hydrazono]-5-methyl-4H-pyrazol-3-ylamine was prepared from 3,4-difluoroaniline (0.62 g, 4.8 mmol) and 3-amino-5-methylpyrazole (0.6 g, 6.2 mmol) according to procedure described above except that the substituted aniline was initially dissolved in a mixture of water (7.2 mL) and DMF (2.0 mL) prior to being acidified. The crude material was initially purified by column chromatography (CH2Cl2:MeOH=20:1). The isolated material was further purified by recrystallization from ethyl acetate/hexanes to yield 0.2 g (18%) of the compound as a yellow solid. MS (m/z, ES+): 238.1 (M+1, 100%).

Workup

  1. customThe crude material was initially purified by column chromatography (CH2Cl2:MeOH=20:1)
  2. customThe isolated material was further purified by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e76301ee69944d8dba22f45fdf82a747
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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