Triethylamine → 6-Chloro-2-[[4-[5-(trifluoromethyl)pyridin-2-yl]-1-piperazinyl]methyl]imidazo[1,2-a]pyridine

HRID 1416276

反応式

HRID 1416276 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH:24]=[C:25]([CH2:27]Cl)[N:26]=2)[CH:23]=1.C(N(CC)CC)C>C(O)CO>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH:24]=[C:25]([CH2:27][N:12]3[CH2:11][CH2:10][N:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][N:7]=4)[CH2:14][CH2:13]3)[N:26]=2)[CH:23]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 6676181-(5-Trifluoromethyl-pyridin-2-yl)-piperazineHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine2 回

生成物 1

HCID 193671176-Chloro-2-[[4-[5-(trifluoromethyl)pyridin-2-yl]-1-piperazinyl]methyl]imidazo[1,2-a]pyridine収率 66.8%

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

A mixture of 1-(5-trifluoromethylpyridin-2-yl)piperazine (0.4803 g), 6-chloro-2-(chloromethyl) imidazo[1,2-a]pyridine (Example 4, Step 1; 0.4177 g), triethylamine (0.231 g), and ethylene glycol (1 mL) is stirred at 80° C. for 70 min. after which additional 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine (0.072 g) is added; thirty minutes later another portion (0.0517 g) is added. After stirring for a total of 2 h, the mixture is cooled and partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. Chromatography on silica gel using methanol/dichloromethane (4/96) and crystallization from ethyl ether/hexane gives 0.549 g of the title compound; mp 81-82° C.; MS m/z 395; IR (mineral oil) 1617, 1332, 1328, 1112, 1082 cm-1. 1H NMR (CDCl3) δ2.68, 3.69, 3.77, 6.62, 7.14, 7.52, 7.55, 7.61, 8.14, 8.38.

後処理

  1. additionis added
  2. additionthirty minutes later another portion (0.0517 g) is added
  3. temperaturethe mixture is cooled
  4. custompartitioned between dichloromethane and aq. sodium bicarbonate
  5. dry with materialThe organic layers are dried over sodium sulfate
  6. concentrationconcentrated
  7. custommethanol/dichloromethane (4/96) and crystallization from ethyl ether/hexane

出典と根拠

ORDレコード
ord-771c779c217e4f72a3f32110133b22b5
出典データセット
uspto-grants-1999_06
特許番号
US05912246

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