Triethylamine → N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide

HRID 245657Notes

Reaction equation

HRID 245657 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:9]([Cl:10])=[N:8][CH:7]=[CH:6][N:5]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[O:42]=[C:43]1[CH2:48][CH2:47][CH:46]([C:49]([O-])=[O:50])[CH2:45][CH2:44]1>ClCCl>[Cl:10][C:9]1[C:4]([CH2:3][NH:2][C:49]([CH:46]2[CH2:47][CH2:48][C:43](=[O:42])[CH2:44][CH2:45]2)=[O:50])=[N:5][CH:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 54601314-OxocyclohexanecarboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 42614233(3-Chloropyrazin-2-yl)methanamine hydrochloride

Product 1

HCID 86674630N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamideYield 104.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-aminomethyl-3-chloropyrazine hydrochloride (3.89 mmol, 0.70 g) in dichloromethane (25 mL) at room temperature was subsequently added triethylamine (7.78 mmol, 1.08 mL), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (4.67 mmol, 1.77 g) and finally 4-oxocyclohexanecarboxylate (3.89 mmol, 553 mg). After stirring for 16 hours, the suspension filtered over decalite. The decalite was washed with dichloromethane. The filtrate was washed with water, dried (sodium sulfate) and concentrated in vacuo. The resulting crude product was purified by column chromatography on silica gel (ethyl acetate). The product was dissolved in dichloromethane, washed with water and concentrated in vacuo to afford 1.09 g of the title compound.

Workup

  1. filtrationthe suspension filtered over decalite
  2. washThe decalite was washed with dichloromethane
  3. washThe filtrate was washed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified by column chromatography on silica gel (ethyl acetate)
  7. dissolutionThe product was dissolved in dichloromethane
  8. washwashed with water
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa3acf190c714b1faa396a1e1c0a9852
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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