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

HRID 1161786Notes

Reaction equation

HRID 1161786 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-eb54832d575d4056b9c77ded62d0c44a
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

Loading…