Triethylamine → 3-oxo-3-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)propanoic acid methyl ester

HRID 909255

Reaction equation

HRID 909255 reaction equation
C[CH:2]([C:6](Cl)=[O:7])[C:3](Cl)=[O:4].[C:9]1([CH:15]2[NH:20][CH2:19][CH2:18][N:17]3[CH:21]=[CH:22][CH:23]=[C:16]23)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN(CC)CC.C(Cl)(Cl)Cl.[C:35](OCC)(=[O:37])C>C(Cl)Cl>[CH3:35][O:37][C:6](=[O:7])[CH2:2][C:3](=[O:4])[N:20]1[CH2:19][CH2:18][N:17]2[CH:21]=[CH:22][CH:23]=[C:16]2[CH:15]1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27709101-phenyl-1H,2H,3H,4H-pyrrolo(1,2-a)pyrazineHCID 10931669MethylmalonylchlorideHCID 21584013Chloroform ethylacetate

Product 1

HCID 674008753-oxo-3-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)propanoic acid methyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (852 μl, 7.9 mmol) of methyl-malonyl chloride in DCM (5 ml) was added dropwise, with vigorous stirring and while cooling (ice-bath), to a solution of (1.5 g, 7.6 mmol) of 1-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine (A2) and (1.27 ml, 9.1 mmol) of NEt3 in DCM (35 ml). Stirring was then carried out for 60 min at RT. The mixture was then washed with water and brine, and the organic phase was dried over MgSO4, filtered and concentrated in vacuo. CC (chloroform/ethyl acetate 10:1) yielded 1.26 g (4.2 mmol, 55%) of 3-oxo-3-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)propanoic acid methyl ester.

Workup

  1. temperaturewhile cooling (ice-bath)
  2. stirringStirring
  3. washThe mixture was then washed with water and brine
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28db2bcd0eb444e0a9ee1d5866be6bc4
Source dataset
uspto-grants-2011_09
Patent number
US08017772B2

Linked notes

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