Formamidine acetate → 6-(2-Chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl ester

HRID 216438Notes

Reaction equation

HRID 216438 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[C:6]([F:12])[C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20].[C:22](O)(=O)C.C(N)=N>CCO.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[C:6]([F:12])[C:7]2[N:11]=[CH:22][NH:10][C:8]=2[CH:9]=1)=[O:21]

Participants

5

Reactant 2

HCID 160693Formamidine acetateHCID 865928784,5-Diamino-2-(2-chloro-phenylamino)-3-fluoro-benzoic acid methyl ester

Product 1

HCID 668977516-(2-Chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4,5-Diamino-2-(2-chloro-phenylamino)-3-fluoro-benzoic acid methyl ester 6a (0.125 g, 0.404 mmol) is suspended in EtOH (2 mL) and formamidine acetate (63 mg, 0.605 mmol) is added. The reaction mixture is heated to reflux. After 16 hours, the reaction mixture is cooled to room temperature and diluted with ethyl acetate. The organic layer is washed with water, saturated NaHCO3, 10% K2CO3 and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give 0.109 g (85%) pure desired product.

Workup

  1. temperatureThe reaction mixture is heated to reflux
  2. washThe organic layer is washed with water, saturated NaHCO3, 10% K2CO3 and brine
  3. dry with materialThe organic layer is dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5133a83e0b0a4f2b8f2bfc9d42d979b5
Source dataset
uspto-grants-2012_06
Patent number
US08193229B2

Reaction notes

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