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Diisopropylethylamine → N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide

HRID 25162
Notes
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Reaction equation

HRID 25162 reaction equation
Cl.[Br:2][C:3]1[N:7]2[CH:8]=[C:9]([C:12]([OH:14])=O)[N:10]=[CH:11][C:6]2=[CH:5][CH:4]=1.[C:15]1([NH2:26])[C:20](F)=[C:19](F)[C:18](F)=[C:17](N)C=1F.Cl.Cl.[CH3:29][CH2:30][N:31](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C1COCC1>[N:26]12[CH2:17][CH2:18][CH:19]([CH2:20][CH2:15]1)[C@@H:30]([NH:31][C:12]([C:9]1[N:10]=[CH:11][C:6]3[N:7]([C:3]([Br:2])=[CH:4][CH:5]=3)[CH:8]=1)=[O:14])[CH2:29]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 697132126-Bromopyrrolo(1,2-a)pyrazine-3-carboxylic acid hydrochloride

Product 1

HCID 10247203
N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-bromopyrrolo[1,2-a]pyrazine-3-carboxylic acid hydrochloride (1.67 mmol), (R)-3-aminoquinulidine dihydrochloride (0.34 g, 1.67 mmol), DIEA (1.5 mL, 8.35 mmol) in DMF (20 mL) and THF (10 mL) is added HATU (0.64 g, 1.67 mmol). The resulting suspension is stirred for 16 h at which time it is concentrated to dryness under reduced pressure. The resulting material is absorbed to silica gel and purified with silica gel chromatography (9% MeOH/1%NH3OH/CH2Cl2 as the eluent) salted with fumeric acid, and crystallized from EtOH/acetone/Et2O to give an off white spheres. Yield 45%. HRMS (FAB) calcd. for C15H17BrN4O+H 349.0664, found 349.0647.

Workup

  1. concentrationis concentrated to dryness under reduced pressure
  2. customThe resulting material is absorbed to silica gel
  3. custompurified with silica gel chromatography (9% MeOH/1%NH3OH/CH2Cl2 as the eluent)
  4. customcrystallized from EtOH/acetone/Et2O
  5. customto give an off white spheres

Sources & evidence

ORD record
ord-719641f08ec94b06a39361fb8608fa61
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858613B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes