p-Toluenesulfonic acid → 1-(2-Chlorophenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-one

HRID 254332

반응식

HRID 254332 반응식
[N:1]1([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:6][CH2:5][C:4](=O)[CH2:3][C:2]1=[O:8].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][CH2:23][C:24](=O)[CH3:25].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[C:4]2[CH2:5][CH2:6][N:1]([N:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[C:2](=[O:8])[C:3]=2[C:24]([CH3:25])=[CH:23]1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 22038474[1,1']Bipiperidinyl-2,4-dioneHCID 220385051-[(2-Chlorophenyl)amino]acetone

생성물 1

HCID 668654341-(2-Chlorophenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-4-one수율 21%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a solution of [1,1′]bipiperidinyl-2,4-dione, from Step 4 (2.49 g, 12.7 mmol) in dry toluene (240 ml) at room temperature were added 1-(2-chlorophenylamino)propan-2-one (2.33 mg, 12.7 mmol) from Step 5 followed by a catalytic amount of p-TSA. The reaction mixture was boiled under reflux with a Dean-Stark trap, and 90 ml toluene was collected in the trap. Then 1 molar equivalent of p-TSA was added and the reaction mixture was boiled under reflux overnight. After cooling to room temperature, the reaction mixture was evaporated and purified by flash chromatography (heptane:EtOAc gradient) to give 0.93 g (21%) of the title compound.

후처리

  1. customwas collected in the trap
  2. additionThen 1 molar equivalent of p-TSA was added
  3. temperatureunder reflux overnight
  4. customthe reaction mixture was evaporated
  5. custompurified by flash chromatography (heptane:EtOAc gradient)

출처 및 근거

ORD 기록
ord-0885863ba76c476f97e9ec65d9808cf7
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875626B2

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