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

HRID 1416293

반응식

HRID 1416293 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e85312339b5a4fbbaac35fb43cdd60ce
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912246

연결된 노트

불러오는 중…