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Fumaric Acid → (RS)-2-(6-methoxy-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate

HRID 864064
Notes
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Reaction equation

HRID 864064 reaction equation
[N:1]([CH:4]([CH3:20])[CH2:5][N:6]1[C:10]2=[CH:11][C:12]3[C:17]([CH2:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[C:9]2[CH:8]=[N:7]1)=[N+]=[N-].[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25]>C(O)C.C(OCC)C.CO.[Pt]=O>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[CH3:19][O:18][C:14]1[CH:13]=[C:12]2[C:17]([CH2:16][CH:15]=1)=[C:9]1[C:10]([N:6]([CH2:5][CH:4]([NH2:1])[CH3:20])[N:7]=[CH:8]1)=[CH:11]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 444972Fumaric AcidHCID 19420937(RS)-1-(2-azido-propyl)-6-methoxy-1,4-dihydro-indeno[2,1-c]pyrazole

Product 1

HCID 19420943(RS)-2-(6-methoxy-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarateYield 86%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 702
Ethanol
Solvent
HCID 887MethanolSolvent
HCID 3283Diethyl EtherSolvent

Procedure

1.58 g (5.86 mmol) of (RS)-1-(2-azido-propyl)-6-methoxy-1,4-dihydro-indeno[2,1-c]pyrazole dissolved in 50 ml of anhydrous ethanol were hydrogenated over 160 mg of platinum oxide for 2 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 680 mg (5.86 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 (86%) of (RS)-2-(6-methoxy-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate (1:1) with m.p. 192°-194° 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-35812cd9fdca4b6d9ac452062e78124c
Source dataset
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05561150

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes