Water → HCID 13022727, compound

HRID 524989Notes

Reaction equation

HRID 524989 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([OH:8])=O.[NH2:9][C:10]1[C:11]([CH3:16])=[CH:12][CH:13]=[CH:14][CH:15]=1.C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C>[C:11]1([CH3:16])[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:6]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7242O-ToluidineHCID 757711-HydroxybenzotriazoleHCID 5743211H-Imidazole-2-carboxylic acid

Product 1

HCID 13022727HCID 13022727, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-imidazole-2-carboxylic acid (0.52 g, 4.64 mmol) in DMF (20 mL) was added o-toluidine (0.50 mL, 4.64 mmol), EDCHCl (1.35 g, 6.96 mmol) and HOBt (0.94 g, 6.96 mmol). The reaction mixture was stirred at room temperature for 16 hours. Then, it was poured into water and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated to dryness. The crude product was purified by flash chromatography (2% to 3% MeOH/DCM) to yield 0.93 g (99%) of the title compound as a beige solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by flash chromatography (2% to 3% MeOH/DCM)

Sources & evidence

ORD record
ord-e5520254fd0446d7b1934bbcb225b175
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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