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

HRID 1925815Notes

Reaction equation

HRID 1925815 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-d718fb806d4f4719b50f5e7a2de3132a
Source dataset
uspto-grants-2012_05
Patent number
US08178693B2

Reaction notes

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