Triethylamine → Ethyl 2-(4-chloropyridin-3-ylamino)-2-oxoacetate

HRID 876799Notes

Reaction equation

HRID 876799 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH2:8].CCN(CC)CC.Cl[C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 5819323-Amino-4-chloropyridine

Product 1

HCID 67306384Ethyl 2-(4-chloropyridin-3-ylamino)-2-oxoacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-chloropyridin-3-amine (R-1) (5 g, 38.9 mmol) in THF (100 mL) was added Et3N (4.72 g, 6.5 mL, 46.7 mmol), followed by ethyl 2-chloro-2-oxoacetate (5.84 g, 4.78 mL, 42.8 mmol) in THF (5 mL) dropwise at 0° C. The resulting mixture was stirred at room temperature for 1 h, and then concentrated in vacuo. The resulting residue was dissolved in EtOAc, and washed with aqueous saturated NaHCO3. The organic layer was separated, dried over Na2SO4, and concentrated to give the title compound, which was used for the next step without further purification. MS (m/z): 229 (M+1)+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in EtOAc
  3. washwashed with aqueous saturated NaHCO3
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-51fa38c81ca84ce98254cbe262dbee36
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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