Hydrochloric Acid → HCID 67425051, compound

HRID 657706Notes

Reaction equation

HRID 657706 reaction equation
Cl.[NH2:2][C:3]([NH2:37])=[N:4][C:5]([C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:20]3[CH2:23][N:22](C(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:21]3)[C:9]=2[CH:8]=1)=[O:6]>[OH-].[Pd+2].[OH-].C(O)C>[NH:22]1[CH2:23][CH:20]([N:10]2[C:9]3[CH:8]=[C:7]([C:5]([N:4]=[C:3]([NH2:37])[NH2:2])=[O:6])[CH:19]=[CH:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:21]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67426045HCID 67426045, compound

Product 1

HCID 67425051HCID 67425051, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A 1.26 ml portion of 1 M hydrochloric acid and 30 mg of 20% palladium hydroxide were added to 9 ml ethanol solution of 300 mg N-(diaminomethylene)-9-[1-(diphenylmethyl)-azetidin-3-yl]-9H-carbazole-2-carboxamide, followed by stirring at room temperature for 4 days under an atmosphere of hydrogen gas. After carrying out celite filtration after adding 1 M sodium hydroxide aqueous solution, the solvent was evaporated, followed by purification by Chromatorex (methanol/chloroform) to obtain 89 mg of 9-azetidin-3-yl-N-(diaminomethylene)-9H-carbazole-2-carboxamide.

Workup

  1. filtrationfiltration
  2. additionafter adding 1 M sodium hydroxide aqueous solution
  3. customthe solvent was evaporated
  4. customfollowed by purification by Chromatorex (methanol/chloroform)

Sources & evidence

ORD record
ord-4abb5e7f134547829e7f74e87e422187
Source dataset
uspto-grants-2011_12
Patent number
US08076348B2

Reaction notes

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