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Fumaric Acid → (RS)-2-(7-fluoro-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate

HRID 864057
Notes
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Reaction equation

HRID 864057 reaction equation
[N:1]([CH:4]([CH3:19])[CH2:5][N:6]1[C:10]2=[CH:11][C:12]3[C:17]([CH2:16][CH:15]=[CH:14][C:13]=3[F:18])=[C:9]2[CH:8]=[N:7]1)=[N+]=[N-].[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]>C(O)C.C(OCC)C.CO.[Pt]=O>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[F:18][C:13]1[CH:14]=[CH:15][CH2:16][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])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 444972Fumaric AcidHCID 19420929(RS)-1-(2-azido-propyl)-7-fluoro-1,4-dihydro-indeno[2,1-c]pyrazole

Product 1

HCID 19420955(RS)-2-(7-fluoro-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarateYield 78.3%

Reagents, catalysts & solvents 4

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

Procedure

1.59 g (6.18 mmol) of (RS)-1-(2-azido-propyl)-7-fluoro-1,4-dihydro-indeno[2,1-c]pyrazole dissolved in 50 ml of anhydrous ethanol were hydrogenated over 160 mg of platinum oxide for 14 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 100 ml of anhydrous diethyl ether, filtered and treated while stirring with a solution of 717 mg (6.18 mmol) of fumaric acid in 10 ml of methanol. The mixture was stirred at room temperature for S hours and the white crystals were subsequently filtered off. 1.68 g (78%) of (RS)-2-(7-fluoro-1,4-dihydroindeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate (1:1) with m.p. 168°-170° 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-ed2789cb8cf34c1c91619ffb45f08341
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