Fumaric Acid → HCID 19420947, compound

HRID 864059Notes

Reaction equation

HRID 864059 reaction equation
[N:1]([CH:4]([CH3:21])[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[F:20])=[C:9]2[CH:8]=[N:7]1)=[N+]=[N-].[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26]>C(O)C.C(OCC)C.CO.[Pt]=O>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[F:20][C:13]1[CH:14]=[CH:15][C:16]([CH3:18])([CH3:19])[C:17]2[C:12]=1[CH:11]=[C:10]1[C:9]=2[CH:8]=[N:7][N:6]1[CH2:5][CH:4]([NH2:1])[CH3:21]

Participants

7

Reactant 2

HCID 444972Fumaric AcidHCID 19420927HCID 19420927, compound

Product 1

HCID 19420947HCID 19420947, compoundYield 83%

Reagents, catalysts & solvents 4

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

Procedure

1.66 g (5.82 mmol) of (RS)-1-(2-azido-propyl)-7-fluoro-4,4-dimethyl-1,4-dihydro-indeno[2,1-c]pyrazole dissolved in 80 ml of anhydrous ethanol were hydrogenated over 160 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 yellow oil obtained was dissolved in 80 ml of anhydrous diethyl ether, filtered and treated while stirring with a solution of 676 mg (5.82 mmol) of fumaric acid in 10 ml of methanol. The mixture was stirred at room temperature for 15 hours and the white crystals were subsequently filtered off. 1.81 g (83%) of (RS)-2-(7-fluoro-4,4-dimethyl-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)- 1-methyl-ethylamine fumarate (1:1) with m.p. 144°-146° were obtained.

Workup

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

Sources & evidence

ORD record
ord-5b6d8837ff1e4f3baa4091664e3f7d18
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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