Piperidine → 2-[4-[4-Piperidinobut-1-ynyl]phenyl]-7-methylimidazo[1,2-a]pyridine

HRID 1268688

반응식

HRID 1268688 반응식
CS(O[CH2:6][CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]3[CH:25]=2)=[CH:12][CH:11]=1)(=O)=O.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+].CO.ClCCl>C(#N)C>[N:26]1([CH2:6][CH2:7][C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]4[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]4[CH:25]=3)=[CH:12][CH:11]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

참가 물질

6

반응물 4

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 220156082-[4-[4-Methanesulfonyloxybut-1-ynyl]phenyl]-7-methylimidazo[1,2-a]pyridine

생성물 1

HCID 101322172-[4-[4-Piperidinobut-1-ynyl]phenyl]-7-methylimidazo[1,2-a]pyridine수율 103.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

The product of Step C (1.00 g) in acetonitrile (15 mL) was treated with piperidine (0.269 g) and potassium carbonate (1.17 g) and heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature, washed with water (20 mL), dried over magnesium sulfate, filtered and evaporated to give crude product. Silica gel chromatography (methanol/dichloromethane) afforded the title compound (1.0 g). MS (ESI) m/z 344.1 (M+H+). 1H NMR (DMSO) δ 8.23 (d, J=6.95 Hz, 1H), 8.15 (s, 1H), 7.73 (d, J=8.37 Hz, 2H), 7.25 (d, J=8.34 Hz, 2H), 7.17 (s, 1H), 6.58 (dd, J=6.9, 1.45 Hz, 1H), 2.33 (m, 6H), 2.23 (b, 2H), 2.18 (s, 3H). 1.33 (pent, 4H), 1.21 (pent, 2H). HRMS: MH+ calcd for C23H26N3, 344.2127. found, 344.2134. Analysis: Calc'd for C23H25N3; C, 80.43; H, 7.34; N, 12.23. Found: C, 80.27; H, 7.15; N, 11.81.

후처리

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. washwashed with water (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product

출처 및 근거

ORD 기록
ord-6049d3cc80df49ef98ac30823c962d4b
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199117B2

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