Triethylamine → HCID 18470852, compound

HRID 2228790Notes

Reaction equation

HRID 2228790 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5](=[O:9])[N:4]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:3]=1[CH3:21].NC[C:24]1[CH:40]=[CH:39][CH:38]=[CH:37][C:25]=1[O:26][CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33].[CH2:41]([N:43](CC)CC)[CH3:42]>C(OCC)(=O)C>[C:32]([O:31][C:30]([NH:29][CH2:28][CH2:27][O:26][C:25]1[CH:24]=[C:40]([CH:39]=[CH:38][CH:37]=1)[CH2:42][CH2:41][NH:43][C:6]1[C:5](=[O:9])[N:4]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:3]([CH3:21])=[C:2]([Cl:1])[N:7]=1)=[O:36])([CH3:33])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 18470839HCID 18470839, compound

Product 1

HCID 18470852HCID 18470852, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preparation 17) (300 mg, 0.92 mmol), tert-butyl 2-[2-(aminomethyl)phenoxy]ethylcarbamate (preparation 128), (257 mg, 0.92 mmol) and triethylamine (140 ml, 1.0 mmol) in ethyl acetate (6 ml) was heated under reflux for 18 hrs. The cooled mixture was partitioned between ethyl acetate (80 ml) and hydrochloric acid (2N, 30 ml) and the phases separated. The organic layer was washed consecutively with hydrochloric acid (2N), saturated NaHCO3 solution, brine, then dried over MgSO4, and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using ethyl acetate:pentane (50:50) as eluant to give the title compound as an orange foam, (500 mg, 95%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hrs
  3. customThe cooled mixture was partitioned between ethyl acetate (80 ml) and hydrochloric acid (2N, 30 ml)
  4. customthe phases separated
  5. washThe organic layer was washed consecutively with hydrochloric acid (2N), saturated NaHCO3 solution, brine
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e6262d010db4440a849240b42ae9d0de
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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