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

HRID 1416293

反応式

HRID 1416293 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:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:24]3[CH2:23][CH2:22][N:21]([C:15]4[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=4[Cl:13])[CH2:26][CH2:25]3)[N:10]=2)[CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27375271-(2,4-Dichlorophenyl)piperazineHCID 116228946-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridine

生成物 1

HCID 193671246-Bromo-2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-bromo-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 15, Step 1; 0.582 g), 1-(2,4-dichlorophenyl)piperazine (Example 31, Step 1; 0.548), triethylamine (Aldrich; 0.288 g), and THF (5 mL) is stirred at 80° C. for 6 h, at which time it is cooled and then partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. Chromatography of the residue on silica gel using methanol/dichloromethane (2/98) and crystallization gives 0.710 g of the title compound; mp 137-138° C.; MS m/z 438, 440; IR (mineral oil) 1479, 1341, 1058, 2810, 803 cm-1. 1H NMR (CDCl3) δ2.78, 3.09, 3.80, 6.96, 7.16-7.23, 7.35, 7.48, 7.55, 8.24.

後処理

  1. temperatureis cooled
  2. custompartitioned between dichloromethane and aq. sodium bicarbonate
  3. dry with materialThe organic layers are dried over sodium sulfate
  4. concentrationconcentrated
  5. custommethanol/dichloromethane (2/98) and crystallization

出典と根拠

ORDレコード
ord-e85312339b5a4fbbaac35fb43cdd60ce
出典データセット
uspto-grants-1999_06
特許番号
US05912246

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