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

HRID 1192603노트

반응식

HRID 1192603 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]([F:21])[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:28].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:28])[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][CH2:18][CH:17]([F:21])[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 583684891-[5-Chloro-8-(3-fluoropiperidin-1-yl)quinolin-7-yl]ethanone

생성물 1

HCID 583686681-[5-Chloro-8-(3-fluoropiperidin-1-yl)quinolin-7-yl]ethanamine

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

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온도
65 °C

실험 절차

A mixture of 1-[5-chloro-8-(3-fluoropiperidin-1-yl)quinolin-7-yl]ethanone (0.0287 g, 0.0936 mmol) and ammonium acetate (0.0721 g, 0.936 mmol) in methanol (1.0 mL) and acetonitrile (1.0 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 (0.234 mL, 0.234 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 C16H20ClFN3 (M+H)+: m/z=308.1; Found: 308.1.

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-67f862a6cabd4ba0badaa442e147f97e
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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