Water → Methyl 1-allyl-7-fluoro-6-(2-fluoro-4-iodophenylamino)-1H-benzo[d]imidazole-5-carboxylate

HRID 558189Notes

Reaction equation

HRID 558189 reaction equation
[CH2:1]([NH:4][C:5]1[C:14]([NH2:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=2[F:24])[C:6]=1[F:25])[CH:2]=[CH2:3].[C:26](O)(=O)C.C(N)=O.C(=O)(O)[O-].[Na+].O>CO>[CH2:1]([N:4]1[C:5]2[C:6]([F:25])=[C:7]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=3[F:24])[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=2[N:15]=[CH:26]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 19966309Formamide acetateHCID 58781154Methyl 4-(allylamino)-5-amino-3-fluoro-2-(2-fluoro-4-iodophenylamino)benzoate

Product 1

HCID 58781150Methyl 1-allyl-7-fluoro-6-(2-fluoro-4-iodophenylamino)-1H-benzo[d]imidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred suspension of methyl 4-(allylamino)-5-amino-3-fluoro-2-(2-fluoro-4-iodophenylamino)benzoate (3.4 g, 7.4 mmoles)) and formamide acetate (3.8 g, 36.4 mmoles) in methanol (30 ml) is heated under reflux for 3 hours. The reaction mixture is cooled to room temperature and a saturated aqueous solution of sodium bicarbonate (30 ml) and water (30 ml) are added. The resulting precipitate is filtered and dried under vacuum to obtain the title compound.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe resulting precipitate is filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-eef908d166944f219b70ad94a137c721
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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