Ammonium Chloride → (9S)-2,3-Dimethyl-9-phenyl-5,6,7,8,9,10-hexahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 584848

반응식

HRID 584848 반응식
[NH2:1][C@H:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6]CC)=O.[CH3:15][C:16]1[N:17]=[C:18]2[C:23](=O)[CH2:22][CH2:21][CH2:20][N:19]2[C:25]=1[CH3:26].CC(C)([O-])C.[K+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH3:15][C:16]1[N:17]=[C:18]2[C:23]3[NH:1][C@H:2]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:3][C:4](=[O:6])[C:22]=3[CH2:21][CH2:20][N:19]2[C:25]=1[CH3:26]

참가 물질

9

반응물 4

HCID 25517Ammonium ChlorideHCID 915085(S)-Ethyl 3-amino-3-phenylpropanoateHCID 113556692,3-dimethyl-5H,6H,7H,8H-imidazo[1,2-a]pyridin-8-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 69288840(9S)-2,3-Dimethyl-9-phenyl-5,6,7,8,9,10-hexahydroimidazo[1,2-h][1,7]naphthyridin-7-one수율 88%

시약·촉매·용매 4

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 962Water용매2회HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

9.7 g (51.6 mmol) of ethyl (S)-3-amino-3-phenylpropionate, 8.5 g (51.6 mmol) of 2,3-dimethyl-6,7-dihydro-5H-imidazo[1,2-a]pyridin-8-one and 0.26 g (1.3 mmol) of p-toluenesulfonic acid monohydrate are heated under reflux in 50 ml of toluene in a water separator. After water no longer separates, the reaction mixture is cooled to 0° C. and diluted with 100 ml of tetrahydrofuran. 7.24 g (64.5 mmol) of potassium tert-butoxide are then introduced and the mixture is stirred at room temperature for 16 h. 150 ml of saturated ammonium chloride solution are added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted with 300 ml of ethyl acetate. The combined organic phases are washed with 250 ml of water, dried over sodium sulfate and evaporated. 13.27 g (88%) of the title compound are isolated as a red-brown oil. An analytical sample is obtained by crystallization using diethyl ether (red solid, m.p. 134° C.).

후처리

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted with 300 ml of ethyl acetate
  3. washThe combined organic phases are washed with 250 ml of water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

출처 및 근거

ORD 기록
ord-f25e5d46ff794a6f94ea1e51118ff4c1
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927292B2

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