Fumaric Acid → HCID 23144389, compound

HRID 337424Notes

Reaction equation

HRID 337424 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>CO.C(O)C.[C].[Pd]>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[O:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[C:15]1[N:16]=[C:17]([NH:19][C:20](=[O:22])[CH3:21])[S:18][C:14]=1[N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 23144191HCID 23144191, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23144389HCID 23144389, compoundYield 19.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Compound 79 (274 mg, 0.72 mmol) was dissolved in methanol (7 mL), and 10% palladium-carbon (274 mg) was added thereto, followed by stirring in an atmosphere of hydrogen at 50° C. for 24 hours. The reaction mixture was filtered through Celite, and the resulting filtrate was concentrated to afford a free form of the entitled Compound. The resulting free form was dissolved in ethanol (5 mL), fumaric acid (83.0 mg, 0.51 mmol) was added thereto, and the precipitated solid was collected by filtration to afford the entitled Compound 80 (40.1 mg, 14%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe resulting filtrate was concentrated
  3. customto afford a free form of the entitled Compound
  4. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-abbae87d50d94a6c8ae4485be3eea640
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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