Hydrochloric Acid → Methyl 2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylate

HRID 1400332노트

반응식

HRID 1400332 반응식
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([NH:11]N)=[CH:7][CH:6]=1.Cl.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.Cl>>[CH3:15][N:16]1[CH2:21][CH2:20][C:19]2[NH:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([O:3][CH3:2])=[O:13])=[CH:10][C:9]=3[C:18]=2[CH2:17]1

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 2788448Methyl 4-hydrazinobenzoate hydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochloride

생성물 1

HCID 1070332Methyl 2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylate

반응 조건

온도
100 °C

실험 절차

Methyl-4-hydrazinylbenzoate hydrochloride (1 equiv.) and 1-methylpiperidin-4-one HCl (0.76-1.4 equiv.) are taken aqueous HCl and heated at 100° C. overnight (the product was detected by LCMS). The reaction mixture is concentrated and refluxed (90° C.) in methanolic HCl overnight (product was detected by LCMS and TLC). The reaction mixture is concentrated and basified with aqueous NaHCO3 solution and extracted with EtOAc. The crude product is crystallized in DCM and ether and hexane.

후처리

  1. concentrationThe reaction mixture is concentrated
  2. temperaturerefluxed (90° C.) in methanolic HCl overnight (product was detected by LCMS and TLC)
  3. concentrationThe reaction mixture is concentrated
  4. extractionextracted with EtOAc
  5. customThe crude product is crystallized in DCM

출처 및 근거

ORD 기록
ord-f238c9c03a834e919f472a94c8800298
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906925B2

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