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

HRID 1929992노트

반응식

HRID 1929992 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.[CH:25]([N:28]1[CH2:33][CH2:32][N:31]([C:34](=[S:36])[NH2:35])[CH2:30][CH2:29]1)([CH3:27])[CH3:26]>CCO>[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3]1[N:35]=[C:34]([N:31]2[CH2:32][CH2:33][N:28]([CH:25]([CH3:27])[CH3:26])[CH2:29][CH2:30]2)[S:36][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 47404374-Propan-2-ylpiperazine-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 579298894-(2,4-Difluorophenyl)-5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-(4-isopropylpiperazin-1-yl)thiazole수율 62.8%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
40 °C

실험 절차

To a solution of 2-bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.49 g, 1.24 mmol, Preparation #A.2) in EtOH (10 μL) was added 4-isopropylpiperazine-1-carbothioamide (0.21 g, 1.12 mmol, Preparation #AO.1.1). The reaction mixture was stirred at about 40° C. for about 2.5 h. The reaction mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. DCM (35 mL) and water (20 mL) were added. The layers were partitioned and the organic layer was washed with additional water (200 mL). The organic layer was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The crude residue was purified by silica gel column chromatography DCM/MeOH (gradient from 100:0 to 90:10) to afford the title compound (0.34 g, 56%) as a yellow solid: LC/MS (Table 1, Method a) Rt=2.06 min; MS m/z: 484.2 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthe solvent was removed under reduced pressure
  3. additionDCM (35 mL) and water (20 mL) were added
  4. customThe layers were partitioned
  5. washthe organic layer was washed with additional water (200 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe crude residue was purified by silica gel column chromatography DCM/MeOH (gradient from 100:0 to 90:10)

출처 및 근거

ORD 기록
ord-80cd74e03ad94d36ba77889ed3ebedcd
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188083B2

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