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1,4-Dioxane → 5-(5-chloro-2-fluoropyridin-4-yl)-3-((tetrahydro-2H-pyran-4-yl)methyl)aminopyrazine-2-carboxamide

HRID 1623336
Notes
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Reaction equation

HRID 1623336 reaction equation
Cl[C:2]1[C:3]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:4][C:5]([C:8]2[C:13]([Cl:14])=[CH:12][N:11]=[C:10]([F:15])[CH:9]=2)=[CH:6][N:7]=1.[C:24]([Cu])#[N:25].[O:27]1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:14][C:13]1[C:8]([C:5]2[N:4]=[C:3]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:2]([C:24]([NH2:25])=[O:27])=[N:7][CH:6]=2)=[CH:9][C:10]([F:15])=[N:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 866506283-chloro-6-(5-chloro-2-fluoropyridin-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amineHCID 178418546HCID 178418546, compound

Product 1

HCID 669370515-(5-chloro-2-fluoropyridin-4-yl)-3-((tetrahydro-2H-pyran-4-yl)methyl)aminopyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

3-chloro-6-(5-chloro-2-fluoropyridin-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (0.0342 g, 0.096 mmol), CuCN (0.034 g, 0.383 mmol), and dppf (0.085 g, 0.153 mmol) were dissolved in dioxane (1.5 ml). The solution was then degassed by sparging with argon for 5 min. It was then treated with Pd2(dba)3 (0.035 g, 0.038 mmol). The reaction mixture was then heated at 100° C. for 5 hr. The reaction mixture was filtered through a pad of Celite then it was concentrated in vacuo to give 0.110 g of 5-(5-chloro-2-fluoropyridin-4-yl)-3-((tetrahydro-2H-pyran-4-yl)methyl)aminopyrazine-2-carboxamide. LCMS (m/z): 366 (MH+), retention time=0.89 min.

Workup

  1. customThe solution was then degassed
  2. customby sparging with argon for 5 min
  3. filtrationThe reaction mixture was filtered through a pad of Celite
  4. concentrationit was concentrated in vacuo

Sources & evidence

ORD record
ord-437fd7c51c664002851a9771d2cfcb75
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778951B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes