Triethylamine → HCID 69961346, compound

HRID 567843Notes

Reaction equation

HRID 567843 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@H:9]1[CH2:14][NH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20](=[O:24])[N:19]([CH2:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:18]=1[CH3:36].C(N(CC)CC)C>C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@H:9]1[CH2:14][NH:15][C:21]1[C:20](=[O:24])[N:19]([CH2:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:18]([CH3:36])=[C:17]([Cl:16])[N:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 28307301HCID 28307301, compound

Product 1

HCID 69961346HCID 69961346, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of [(3R)-4-benzylmorpholinyl]methylamine (preparation 95) (4.2 g, 20.4 mmol), benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preparation 17) (1 g, 3.06 mmol), and triethylamine (0.7 ml, 5.0 mmol) in ethyl acetate (25 ml) was heated under reflux for 18 hrs. The cooled reaction mixture was diluted with ethyl acetate, washed with water, then brine, dried over MgSO4 and concentrated under reduced pressure. The residual brown oil was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (0:100 to 100:0) to give the title compound as a white solid, (500 mg, 32%).

Workup

  1. temperatureunder reflux for 18 hrs
  2. customThe cooled reaction mixture
  3. washwashed with water
  4. dry with materialbrine, dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residual brown oil was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (0:100 to 100:0)

Sources & evidence

ORD record
ord-ea4ff7c65d2c49d59a31761049ca6527
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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