Tetrahydrofuran → 1-[5-Chloro-8-(3-methoxypiperidin-1-yl)quinolin-7-yl]ethanamine

HRID 1192616노트

반응식

HRID 1192616 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][CH2:18][CH:17]([O:21][CH3:22])[CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:29])[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][CH2:18][CH:17]([O:21][CH3:22])[CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 583684851-[5-Chloro-8-(3-methoxypiperidin-1-yl)quinolin-7-yl]ethanone

생성물 1

HCID 583686401-[5-Chloro-8-(3-methoxypiperidin-1-yl)quinolin-7-yl]ethanamine

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

반응 조건

온도
65 °C

실험 절차

A mixture of 1-[5-chloro-8-(3-methoxypiperidin-1-yl)quinolin-7-yl]ethanone (0.0373 g, 0.117 mmol) and ammonium acetate (0.0902 g, 1.17 mmol) in methanol (0.5 mL) and acetonitrile (0.5 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.29 mL, 0.29 mmol). The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C17H23ClN3O (M+H)+: m/z=320.2; Found: 320.1.

후처리

  1. temperatureAfter cooling to room temperature, to the resulting mixture
  2. temperatureThe reaction was heated at 65° C. overnight
  3. temperatureThe mixture was cooled to room temperature
  4. customquenched with sat. NaHCO3 solution
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ccca6b2cecf84583ab14cbad3671b5b4
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

반응 노트

불러오는 중…