Dimethylamine → 5-chloro-N,N-dimethylpyrazine-2-carboxamide

HRID 2425480Notes

Reaction equation

HRID 2425480 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[N:9]=[CH:10][C:11]([C:14]([OH:16])=O)=[N:12][CH:13]=1.[CH3:17][NH:18][CH3:19].C(N(CC)CC)C>ClCCl.CN(C=O)C>[Cl:7][C:8]1[N:9]=[CH:10][C:11]([C:14]([N:18]([CH3:19])[CH3:17])=[O:16])=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 4654725-Chloropyrazinoic acid

Product 1

HCID 590004705-chloro-N,N-dimethylpyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (1.7 mL, 19 mmol) was added to a suspension of 5-chloropyrazine-2-carboxylic acid (CAS no. 36070-80-1) (2.53 g, 16.0 mmol) in dichloromethane (25 mL) and DMF (4 drops) at RT and under argon. The mixture was allowed to stir for 1.5 h, concentrated in vacuo to and the residue was re-dissolved in dichloromethane (25 mL). Dimethylamine (2M in THF, 8.77 mL, 17.6 mmol) was then added dropwise followed by triethylamine (4.9 mL, 35 mmol) and allowed to stir for a further 5.5 hours. The reaction mixture was concentrated in vacuo and the residue was re-dissolved in dichloromethane and filtered. The filtrate was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexanes to give the desired compound (1.88 g).

Workup

  1. customat RT
  2. concentrationconcentrated in vacuo to and the residue
  3. dissolutionwas re-dissolved in dichloromethane (25 mL)
  4. stirringto stir for a further 5.5 hours
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. dissolutionthe residue was re-dissolved in dichloromethane
  7. filtrationfiltered
  8. customThe filtrate was chromatographed on silica
  9. washeluting with a gradient of 50-100% ethyl acetate in isohexanes

Sources & evidence

ORD record
ord-01594a91a17c4a54bf777a9abf925e2b
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

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