Fumaric Acid → HCID 86749889, compound

HRID 864051Notes

Reaction equation

HRID 864051 reaction equation
[N:1]([CH:4]([CH3:22])[CH2:5][N:6]1[C:10]2=[CH:11][C:12]3[C:17]([CH2:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])=[C:9]2[C:8]([O:20][CH3:21])=[N:7]1)=[N+]=[N-].[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>C(O)C.C(OCC)C.CO.[Pt]=O>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[CH3:21][O:20][C:8]1[C:9]2[C:10](=[CH:11][C:12]3[C:17]=2[CH2:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])[N:6]([CH2:5][C@@H:4]([NH2:1])[CH3:22])[N:7]=1

Participants

7

Reactant 2

HCID 444972Fumaric AcidHCID 19420959HCID 19420959, compound

Product 1

HCID 86749889HCID 86749889, compoundYield 46%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1.11 g (3.71 mmol) of (RS)-1-(2-azido-propyl)-3,7-dimethoxy-1,4-dihydro-indeno[2,1-c]pyrazole dissolved in 60 ml of anhydrous ethanol were hydrogenated over 110 mg of platinum oxide for 1.5 hours. The catalyst was subsequently filtered off, rinsed with ethanol and the solvent was removed in a vacuum. The colorless oil obtained was dissolved in 50 ml of anhydrous diethyl ether, filtered and treated while stirring with a solution of 430 mg (3.71 mmol) of fumaric acid in 5 ml of methanol. The mixture was stirred at room temperature for 15 hours and the beige crystals were subsequently filtered off. 0.56 g (46%) of (S)-2-(3,7-dimethoxy-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate (1:05) with m.p. 209° was obtained.

Workup

  1. filtrationThe catalyst was subsequently filtered off
  2. washrinsed with ethanol
  3. customthe solvent was removed in a vacuum
  4. customThe colorless oil obtained
  5. filtrationfiltered
  6. additiontreated
  7. filtrationthe beige crystals were subsequently filtered off

Sources & evidence

ORD record
ord-e15ab1dc92b74c72ada586eeb51bcdc3
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

Loading…