Triethylamine → HCID 22179411, compound

HRID 1016256Notes

Reaction equation

HRID 1016256 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][N:12]1[C:17]([CH3:18])=[C:16]([Cl:19])[N:15]=[C:14](Cl)[C:13]1=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28][NH2:29])=[CH:25][CH:24]=1.C(N(CC)CC)C>C(OCC)(=O)C>[C:23]1([CH3:22])[CH:31]=[CH:30][C:26]([CH2:27][CH2:28][NH:29][C:14]2[C:13](=[O:21])[N:12]([CH2:11][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[C:17]([CH3:18])=[C:16]([Cl:19])[N:15]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76751p-MethylphenethylamineHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate

Product 1

HCID 22179411HCID 22179411, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-benzyloxycarbonylmethyl-3,5-dichloro-6-methylpyrazinone (656 mg, 2.00 mmol), as prepared in the preceding step, 4-methylphenethylamine (380 mg, 2.81 mmol), triethylamine (405 mg, 4.01 mmol), and ethyl acetate (20 mL) was refluxed overnight. After cooling to room temperature, the solution was washed with 10% citric acid (×2). The aqueous solutions were back extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and contracted to give the title compound as a yellow solid (854 mg, 100%). 1H NMR (CDCl3) δ 7.38-7.32 (m, 5H), 7.12 (s, 4H), 6.09 (s, 1H), 5.21 (s, 2H), 4.79 (s, 2H), 3.65 (dd, 2H, J=7.0, 13.0 Hz), 2.88 (t, 2H, J=7.1 Hz), 2.32 (s, 3H), 2.21 (s, 3H).

Workup

  1. temperaturewas refluxed overnight
  2. washthe solution was washed with 10% citric acid (×2)
  3. extractionThe aqueous solutions were back extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried (Na2SO4)

Sources & evidence

ORD record
ord-21337287f0204f0287a7d9b2af884dd3
Source dataset
uspto-grants-2002_11
Patent number
US06476016B2

Reaction notes

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