Triethylamine → HCID 69761928, compound

HRID 658481Notes

Reaction equation

HRID 658481 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](Cl)=[O:10])[CH:4]=1.Cl.NC[C:15]([NH:17][CH3:18])=[O:16].[CH2:19]([N:21](CC)CC)C>C1COCC1.C(#N)C>[CH3:19][NH:21][C:15]([N:17]([CH3:18])[C:9]([C:5]1[CH:4]=[C:3]([Cl:2])[CH:8]=[CH:7][N:6]=1)=[O:10])=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 138422022-amino-N-methylacetamide hydrochlorideHCID 223972704-Chloropyridine-2-carbonyl chloride--hydrogen chloride (1/1)

Product 1

HCID 69761928HCID 69761928, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloropyridine-2-carbonyl choride HCl (2.00 g, 9.41 mmol) in THF (16.4 mL) and acetonitrile (9.4 mL) was added 2-amino-N-methylacetamide hydrochloride (1.29 g, 10.35 mmol, 1.1 eq) and triethylamine (5.25 mL, 37.6 mmol, 4.0 eq) at 0° C. The resulting dark brown reaction mixture was stirred at RT for 2 h. The volatile solvent was removed under reduced pressure, and the residue was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified on MPLC (biotage) eluted with 100% EtOAc to give 1.4 g (65.3%) of 4-chloropyridine-2-carboxylic acid methylcarbamoyl-N-methylamide as a tan solid: TLC (75% EtOAc/hex), Rf=0.14; MS LC-MS [M+H]+=228.

Workup

  1. customThe volatile solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified on MPLC (biotage)
  8. washeluted with 100% EtOAc

Sources & evidence

ORD record
ord-f79bdb24e1824ec99d62f8d9445561bf
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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