O-Phenylenediamine → HCID 59028486, compound

HRID 2369837Notes

Reaction equation

HRID 2369837 reaction equation
CCN=C=NCCCN(C)C.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19].[C:20]1([C:26]2[CH:30]=[C:29]([C:31](O)=[O:32])[NH:28][N:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:31]([C:29]1[NH:28][N:27]=[C:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:30]=1)=[O:32]

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 121025Pyrazole-5-carboxylic acid, 3-phenyl-

Product 1

HCID 59028486HCID 59028486, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDCI (288 mg, 1.5 mmol) was added to a solution of 1,2-diaminobenzene (0.141 g, 1.31 mmol), 3-phenyl-1H-pyrazole-5-carboxylic acid (188 mg, 1.0 mmol) and HOBT (203 mg, 1.5 mmol) in anhydrous DMF (5 mL). The reaction was stirred under nitrogen at room temperature. After twelve hours the reaction was concentrated in vacuo and precipitated from methanol with a small amount of water. The solid was collected by vacuum filtration and further purified on reverse phase HPLC using water-acetonitrile gradient (0.1% TFA) to provide the corresponding amide (60 mg, 38% yield).

Workup

  1. concentrationAfter twelve hours the reaction was concentrated in vacuo
  2. customprecipitated from methanol with a small amount of water
  3. filtrationThe solid was collected by vacuum filtration
  4. customfurther purified on reverse phase

Sources & evidence

ORD record
ord-62078163068f47c1b900a24054c6e75b
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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