P-Toluic Acid → HCID 71060929, compound

HRID 1771138Notes

Reaction equation

HRID 1771138 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:23][C:24]1[S:28][C:27]([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[N:26][C:25]=1[C:35]([NH2:37])=[O:36]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:23][C:24]2[S:28][C:27]([C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[N:26][C:25]=2[C:35]([NH2:37])=[O:36])=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7470P-Toluic AcidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 70515320HCID 70515320, compound

Product 1

HCID 71060929HCID 71060929, compoundYield 32.46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

4-Methylbenzoic acid (0.054 g, 0.0004 mol) and carbonyl di-imidazole (CDI) (0.097 g 0.0006 mol), are dissolved in dry DMF (2 ml) and stirred at 90° C. for 1 hr, then 5-amino-2-pyridin-4-yl-thiazole-4-carboxylic acid amide (0.05 g, 0.0002 mol) is added and the mixture is stirred overnight at 90° C. After the completion of the reaction is evidenced from TLC, solvent is evaporated and the crude product is purified by silica gel column chromatography to afford 17.6 mg 5-(4-methyl-benzoylamino)-2-pyridin-4-yl-thiazole-4-carboxylic acid amide (“A55”) (17.6 mg, 32.46% yield);

Workup

  1. stirringthe mixture is stirred overnight at 90° C
  2. customis evaporated
  3. customthe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-454ef8ea2e4a4e6d976c18871ee18426
Source dataset
uspto-grants-2016_02
Patent number
US09249114B2

Reaction notes

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