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

HRID 1416252

반응식

HRID 1416252 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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.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:23]3[CH2:22][CH2:21][N:20]([C:17]4[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=4)[CH2:25][CH2:24]3)[N:10]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

생성물 1

HCID 193671366-Chloro-2-[[4-(4-fluorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine수율 77%

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2-(chloromethyl)-6-chloroimidazo[1,2-a]pyridine (Example 4, Step 1; 0.50 g), 1-(4-fluorophenyl)piperazine (Aldrich; 0.471 g), triethylamine (0.277 g), and ethylene glycol (2 mL) is stirred at 80° C. for 1.3 h. After cooling, the mixture is partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and the filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (2/98) and the appropriate fractions are combined and concentrated. The resulting material is crystallized from dichloromethane/hexane to give 0.66 g of the title compound; mp 129.5-131° C.; MS m/z at 344; IR (mineral oil) 1511, 1236, 1330, 1325, 825 cm-1; 1 H NMR (CDCl3) δ2.74, 3.15, 6.86-6.98, 7.13, 7.52, 7.54, 8.14.

후처리

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between dichloromethane and aq. sodium bicarbonate
  3. dry with materialThe organic layers are dried over sodium sulfate
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel
  6. concentrationconcentrated
  7. customThe resulting material is crystallized from dichloromethane/hexane

출처 및 근거

ORD 기록
ord-7f6fbb05510c4460bc7c44b5446dd088
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912246

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