Formic Acid → 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid

HRID 1667698Notes

Reaction equation

HRID 1667698 reaction equation
[C:1]([C:4]1[S:8][C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=2[N+:19]([O-])=O)[C:13]([OH:15])=[O:14])=[N:6][C:5]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)(=[O:3])[NH2:2].[CH:29](O)=O>[Pd]>[C:1]([C:4]1[S:8][C:7]([N:9]2[C:10]3[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[CH:16]=[CH:17][C:18]=3[N:19]=[CH:29]2)=[N:6][C:5]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 866428143-[5-Carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-4-nitro-benzoic acid

Product 1

HCID 674273413-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 0.280 g (0.67 mmole) of 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-4-nitro-benzoic acid (VI.10), 0.20 g of 10% palladium on carbon catalyst and 3 mL of 96% formic acid was stirred under an atmosphere of hydrogen at room temperature for 16 hours. The mixture was filtered through Diatomaceous earth and the Diatomaceous earth pad was washed with formic acid. The filtrate was concentrated under reduced pressure and the residue was dissolved in 1 mL of tetrahydrofuran and then added dropwise to 50 mL of water. The solid was collected by filtration, washing with water, to give 0.163 g of 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (I.10a).

Workup

  1. filtrationThe mixture was filtered through Diatomaceous earth
  2. washthe Diatomaceous earth pad was washed with formic acid
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 1 mL of tetrahydrofuran
  5. additionadded dropwise to 50 mL of water
  6. filtrationThe solid was collected by filtration
  7. washwashing with water

Sources & evidence

ORD record
ord-eee7e49b7e234f43a2b54a199f40d386
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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