Triethylamine → 6-Chloro-2-[[4-(3-chloro4-methoxyphenyl)-1-piperazinyl]-methyl]imidazo[1,2-a]pyridine

HRID 1416295

反応式

HRID 1416295 の反応式
[Cl: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:15]=[C:16]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C(N(CC)CC)C>C(O)CO>[Cl: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:16]4[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([Cl:13])[CH:15]=4)[CH2:27][CH2:26]3)[N:10]=2)[CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 47395621-(3-Chloro-4-methoxyphenyl)piperazineHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine3 回

生成物 1

HCID 193671516-Chloro-2-[[4-(3-chloro4-methoxyphenyl)-1-piperazinyl]-methyl]imidazo[1,2-a]pyridine収率 62%

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

A mixture of 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 4, Step 1; 0.290 g), 1-(3-chloro-4-methoxyphenyl)piperazine (0.271 g), triethylamine (Aldrich; 0.159 g), and ethylene glycol (2 mL) is stirred at 80° C. for 40 min, at which time another 0.031 g of 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine is added; after another 45 min, an additional 0.025 g of 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine is added. When the mixture has stirred for a total of 2 h, it is cooled and partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel using methanol/dichloromethane (2/98) to give 0.29 g of the title compound after crystallization from ethyl acetate/hexane; mp 99-100.5 ° C.; MS m/z 390, 392; IR (mineral oil) 1510, 1501, 795, 1072, 1321 cm-1. 1H NMR (CDCl3) δ2.75, 3.14, 3.78, 3.84, 6.83, 6.97, 7.13, 7.52, 7.55, 8.14.

後処理

  1. additionis added
  2. temperatureis cooled
  3. custompartitioned between dichloromethane and aq. sodium bicarbonate
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel

出典と根拠

ORDレコード
ord-bbdc27d318ee48a6983a436b69eb9cb9
出典データセット
uspto-grants-1999_06
特許番号
US05912246

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