Triethylamine → 6-Bromo-2-[[4-(4-chlorophenyl)-1-piperazinyl]methyl]imidazo[1,2-a]pyridine

HRID 1416265

反応式

HRID 1416265 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.Cl.Cl.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C(N(CC)CC)C>C(O)CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:25]3[CH2:24][CH2:23][N:22]([C:19]4[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=4)[CH2:27][CH2:26]3)[N:10]=2)[CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 116228946-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridineHCID 12212341Piperazine, 1-(4-chlorophenyl)-, hydrochloride (1:2)

生成物 1

HCID 193671286-Bromo-2-[[4-(4-chlorophenyl)-1-piperazinyl]methyl]imidazo[1,2-a]pyridine

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-bromo-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 15, Step 1; 0.3042 g), 1-(4-chlorophenyl)piperazine dihydrochloride (Aldrich; 0.3708 g), triethylamine (Aldrich; 0.55 mL), and ethylene glycol (5.6 mL) is stirred for 1 h at 80° C. After cooling, the mixture is partitioned between water and dichloromethane. The combined organic layers are washed with brine, dried with MgSO4, and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96) to give, after crystallization from ethyl acetate/methanol/dichlormetane, 0.1756 g of the title compound; mp 154-155° C.; MS m/z 404, 406, 408; IR (mineral oil) 1495, 1500, 1224, 823, 812 cm-1 ; 1H NMR (CDCl3) δ2.72, 3.19, 3.76, 6.83, 7.20, 7.22, 7.47, 7.52, 8.24.

後処理

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between water and dichloromethane
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. customto give
  8. customafter crystallization from ethyl acetate/methanol/dichlormetane, 0.1756 g of the title compound

出典と根拠

ORDレコード
ord-94e86b75667d4d1f9cf7e59f8190eb74
出典データセット
uspto-grants-1999_06
特許番号
US05912246

関連ノート

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