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Propyne → N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-prop-1-ynylpyrrolo[1,2-a]pyrazine-3-carboxamide Tartrate

HRID 25163
Notes
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Reaction equation

HRID 25163 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[N:13]=[CH:14][C:15]3[N:16]([C:18](Br)=[CH:19][CH:20]=3)[CH:17]=1)=[O:11])[CH2:2]2.[C:22](P(C(C)(C)C)C(C)(C)C)(C)([CH3:24])[CH3:23].C#CC.[C:38]([OH:47])(=[O:46])[C@H:39]([C@@H:41]([C:43]([OH:45])=[O:44])[OH:42])[OH:40]>C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.[I+].[Cu+].O1CCOCC1>[C:43]([CH:41]([CH:39]([C:38]([OH:47])=[O:46])[OH:40])[OH:42])([OH:45])=[O:44].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[N:13]=[CH:14][C:15]3[N:16]([C:18]([C:23]#[C:22][CH3:24])=[CH:19][CH:20]=3)[CH:17]=1)=[O:11])[CH2:2]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6335PropyneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 439655D-Tartaric acidHCID 10247203N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide

Product 1

HCID 69771992N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-prop-1-ynylpyrrolo[1,2-a]pyrazine-3-carboxamide TartrateYield 5%

Reagents, catalysts & solvents 3

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 178505377HCID 178505377, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To an argon purged mixture of dichlorobis(benzonitrile)palladium (II) (0.085 g, 0.22 mmol) and copper (I) iodine (0.124 g, 0.65 mmol) is added, N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide (0.641 g, 1.8 mmol) and dioxane (20 mL). The suspension is sparged with argon, and diiopropylamine (0.30 mL, 1.5 mmol), tri tert-butyl phosphine (0.064 g, 0.32 mmol) and condensed propyne (excess) is added. The reaction vessel is quickly sealed and stirred at rt for 15 h at which point it is filtered through a plug of celite, concentrated to dryness, and the residue dissolved in CHCl3 (150 mL) that is washed with a solution containing 1:1 NH4OH/brine (5×35 mL). The crude oil is purified using preparative HPLC to give a yellow oil that is salted with d-tartaric acid, and crystallized from EtOH/Et2O to give a pale yellow solid. Yield 5%. HRMS (FAB) calcd for C18H20N4O+H 309.1715, found 309.1715.

Workup

  1. customTo an argon purged
  2. additionis added
  3. additionis added
  4. customThe reaction vessel is quickly sealed
  5. filtrationis filtered through a plug of celite,
  6. concentrationconcentrated to dryness
  7. dissolutionthe residue dissolved in CHCl3 (150 mL) that
  8. washis washed with a solution
  9. additioncontaining 1:1 NH4OH/brine (5×35 mL)
  10. customThe crude oil is purified
  11. customto give a yellow oil that
  12. customcrystallized from EtOH/Et2O
  13. customto give a pale yellow solid

Sources & evidence

ORD record
ord-e72a30d1a81d43dfbedd129a2f14c0e8
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858613B2

Reaction notes

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