Hydrochloric Acid → HCID 15885492, compound

HRID 1358455Notes

Reaction equation

HRID 1358455 reaction equation
ON1C2N=CC=CC=2N=N1.CCN=C=NCCCN(C)C.[C:22]([O:26][C:27]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=O)=[CH:32][CH:31]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23].[C:39]1([S:45]([NH:48][NH2:49])(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.Cl>CN(C)C=O>[C:39]1([S:45]([NH:48][NH:49][C:34]([C:33]2[CH:32]=[CH:31][C:30]([NH:29][C:27](=[O:28])[O:26][C:22]([CH3:23])([CH3:24])[CH3:25])=[CH:38][CH:37]=2)=[O:36])(=[O:46])=[O:47])[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 65723Benzenesulfonyl hydrazideHCID 181649HOAtHCID 27559314-{[(Tert-butoxy)carbonyl]amino}benzoic acid

Product 1

HCID 15885492HCID 15885492, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.1 mmol (1.65 g) of 1-hydroxy-7-azabenzotriazole and 18 mmol (3.45 g) of EDCI are added in succession to a solution of 12 mmol (2.85 g) of 4-[(tert-butoxycarbonyl)amino]benzoic acid in 20 ml of dimethylformamide. The reaction mixture is stirred at room temperature for one hour, and 18 mmol (3.1 g) of benzenesulphonohydrazide are added. After stirring for eight hours at room temperature, the reaction mixture is poured into 100 ml of a 10% hydrochloric acid solution and extracted four times with 50 ml of ethyl acetate. The organic phase is washed twice with 50 ml of water and then three times with an aqueous saturated sodium hydrogen carbonate solution and once with 50 ml of an aqueous saturated sodium chloride solution. After drying over magnesium sulphate, filtration and concentration, the expected product is obtained.

Workup

  1. stirringAfter stirring for eight hours at room temperature
  2. extractionextracted four times with 50 ml of ethyl acetate
  3. washThe organic phase is washed twice with 50 ml of water
  4. dry with materialAfter drying over magnesium sulphate, filtration and concentration

Sources & evidence

ORD record
ord-73267cd14e75470a80779e6dae86c9a2
Source dataset
uspto-grants-2003_07
Patent number
US06596749B2

Reaction notes

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