3-amino-5-(4-fluorophenyl)thiophene-2-carboxylic Acid → 3-[3-(2-Chloro-4,5-difluorobenzoyl)ureido]-5-(4-fluorophenyl)thiophene-2-carboxylic acid

HRID 460319Notes

Reaction equation

HRID 460319 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([OH:16])=[O:15].[Cl:17][C:18]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:19]=1[C:20]([N:22]=[C:23]=[O:24])=[O:21]>C(#N)C>[Cl:17][C:18]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:19]=1[C:20]([NH:22][C:23](=[O:24])[NH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[S:4][C:3]=1[C:14]([OH:16])=[O:15])=[O:21]

Participants

4

Reactant 2

HCID 107523413-amino-5-(4-fluorophenyl)thiophene-2-carboxylic AcidHCID 115575832-Chloro-4,5-difluorobenzoyl Isocyanate

Product 1

HCID 98252113-[3-(2-Chloro-4,5-difluorobenzoyl)ureido]-5-(4-fluorophenyl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-Amino-5-(4-fluorophenyl)thiophene-2-carboxylic acid (50 mg) is initially charged in 3 ml of acetonitrile. The equimolar solution of 2-chloro-4,5-difluorobenzoyl isocyanate in acetonitrile is added and the mixture is stirred at RT. After 3 hours, the solid is filtered off with suction, stirred once more with methanol, filtered off with suction and dried under reduced pressure.

Workup

  1. filtrationthe solid is filtered off with suction
  2. stirringstirred once more with methanol
  3. filtrationfiltered off with suction
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-7d6ed84ca93941778ad9a7a317901dbe
Source dataset
uspto-grants-2007_03
Patent number
US07196114B2

Reaction notes

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