Fumaric Acid → HCID 86749885, compound

HRID 864038Notes

Reaction equation

HRID 864038 reaction equation
[N:1]([C@@H:4]([CH3:22])[CH2:5][N:6]1[C:10]2=[CH:11][C:12]3[C:17]([C:16]([CH3:19])([CH3:18])[CH:15]=[CH:14][C:13]=3[O:20][CH3:21])=[C:9]2[CH:8]=[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:13]1[CH:14]=[CH:15][C:16]([CH3:19])([CH3:18])[C:17]2[C:12]=1[CH:11]=[C:10]1[C:9]=2[CH:8]=[N:7][N:6]1[CH2:5][C@@H:4]([NH2:1])[CH3:22]

Participants

7

Reactant 2

HCID 444972Fumaric AcidHCID 86749884HCID 86749884, compound

Product 1

HCID 86749885HCID 86749885, compoundYield 69%

Reagents, catalysts & solvents 4

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

Procedure

1.38 g (4.6 mmol) of (S)-1-(2-azido-propyl)-7-methoxy-4,4-dimethyl-1,4-dihydro-indeno[2,1-c]pyrazole dissolved in 50 ml of anhydrous ethanol were hydrogenated over 140 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 80 ml of anhydrous diethyl ether, filtered and treated while stirring with a solution of 534 mg (4.6 mmol) of fumaric acid in 10 ml of methanol. The mixture was stirred at room temperature for 18 hours and the white crystals were subsequently filtered off. 1.23 g (69%) of (S)-2-(7-methoxy-4,4-dimethyl-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate (1:1) with m.p. 160°-162° were 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 white crystals were subsequently filtered off

Sources & evidence

ORD record
ord-f755a52e32ff429e9c1a6510ff251280
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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