Triethylamine → HCID 59900521, compound

HRID 567859Notes

Reaction equation

HRID 567859 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:28]=[CH:29][CH:30]=1)[O:14][CH2:15][C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[Cl:31][C:32]1[N:37]=[C:36](Cl)[C:35](=[O:39])[N:34]([CH2:40][C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])[C:33]=1[CH3:51]>C(OCC)(=O)C>[CH2:44]([O:43][C:41](=[O:42])[CH2:40][N:34]1[C:33]([CH3:51])=[C:32]([Cl:31])[N:37]=[C:36]([NH:8][CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([CH:28]=[CH:29][CH:30]=2)[O:14][CH2:15][C@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[C:35]1=[O:39])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 54408569HCID 54408569, compound

Product 1

HCID 59900521HCID 59900521, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.51 ml, 3.67 mmol) was added to a solution of tert-butyl (2R)-2-{[3-(2-aminoethyl)phenoxy]methyl}-1-pyrrolidinecarboxylate (preparation 134) (588 mg, 1.84 mmol) and benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preparation 17) (60 mg, 1.83 mmol) in ethyl acetate (10 ml), and the reaction heated under reflux for 6 hrs. The cooled mixture was partitioned between water and ethyl acetate, and the layers separated. The organic phase was washed with water, then brine, dried over MgSO4 and evaporated under reduced pressure to give the title compound, (1.07 g, 94%).

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 6 hrs
  3. customThe cooled mixture was partitioned between water and ethyl acetate
  4. customthe layers separated
  5. washThe organic phase was washed with water
  6. dry with materialbrine, dried over MgSO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dc7b76a0d3384bdf94114eccadfc7fd1
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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