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

HRID 8379

反応式

HRID 8379 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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, 1 H), 8.15 (s, 1 H), 7.73 (d, J=8.37 Hz, 2 H), 7.25 (d, J=8.34 Hz, 2 H), 7.17 (s, 1 H), 6.58 (dd, J=6.9, 1.45 Hz, 1H), 2.33 (m, 6 H), 2.23 (b, 2 H), 2.18 (s, 3 H). 1.33 (pent, 4 H), 1.21 (pent, 2 H). 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.

後処理

  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

出典と根拠

ORDレコード
ord-6414fe018863447e9a234c42b7b4c928
出典データセット
uspto-grants-2006_08
特許番号
US07087757B2

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