Hydrazine hydrate (1:1) → 6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid hydrazide

HRID 216553Notes

Reaction equation

HRID 216553 reaction equation
C[O:2][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[CH3:22])=[C:12]([F:23])[C:8]2[NH:9][CH:10]=[N:11][C:7]=2[CH:6]=1)=O.O.[NH2:25][NH2:26]>CCO>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:13]2[C:5]([C:3]([NH:25][NH2:26])=[O:2])=[CH:6][C:7]3[NH:11][CH:10]=[N:9][C:8]=3[C:12]=2[F:23])=[C:16]([CH3:22])[CH:17]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178497004HCID 178497004, compound

Product 1

HCID 668979206-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid hydrazideYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl ester 8a (0.051 g, 0.135 mmol) is suspended in EtOH (5 mL) and hydrazine hydrate (0.118 g, 2.023 mmol) is added. The reaction mixture is heated at reflux for 16 hours. The reaction mixture is concentrated under reduced pressure and purified by FCC eluted with 97:3 ethyl acetate:MeOH to give 0.041 g (81%) of clean desired product: LC/MS ESI (+) m/z 378, 380 (M+ Br pattern) detected.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. custompurified by FCC
  5. washeluted with 97:3 ethyl acetate

Sources & evidence

ORD record
ord-881bd24c14214824a40ad8e0367cbf0f
Source dataset
uspto-grants-2012_06
Patent number
US08193230B2

Reaction notes

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