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

HRID 909255노트

반응식

HRID 909255 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-28db2bcd0eb444e0a9ee1d5866be6bc4
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017772B2

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