Piperidine-1-carbothioamide → 4-(2,4-Difluorophenyl)-5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-(piperidin-1-yl)thiazole

HRID 1929991노트

반응식

HRID 1929991 반응식
Br[CH:2]([C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([CH:22]([CH3:24])[CH3:23])=[N:20][N:21]=2)[N:18]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=O.[N:25]1([C:31](=[S:33])[NH2:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CCO>[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3]1[N:32]=[C:31]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[S:33][C:2]=1[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([CH:22]([CH3:24])[CH3:23])=[N:20][N:21]=2)[N:18]=1

참가 물질

4

반응물 2

HCID 1551232Piperidine-1-carbothioamideHCID 579298612-Bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

생성물 1

HCID 579299704-(2,4-Difluorophenyl)-5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-(piperidin-1-yl)thiazole수율 39%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.250 g, 0.632 mmol; Preparation #A.2) and piperidine-1-carbothioamide (Oakwood Products Inc., 0.082 g, 0.57 mmol) in EtOH (3 mL) was heated to reflux for about 3 h. After cooling to ambient temperature, the crude mixture was partitioned between DCM and water. The organics were dried over MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel chromatography using heptane/EtOAc (linear gradient, 50:50 to 0:100) to give the title compound (0.098 g, 35%): LC/MS (Table 1, Method a) Rt=4.18 min; MS m/z: 441.8 (M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for about 3 h
  3. customthe crude mixture was partitioned between DCM and water
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-92d717cd8b5c411da3d75d88fc15cb9d
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188083B2

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