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

HRID 1416295

반응식

HRID 1416295 반응식
[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

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 47395621-(3-Chloro-4-methoxyphenyl)piperazineHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine3회

생성물 1

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

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bbdc27d318ee48a6983a436b69eb9cb9
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912246

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