Tetrahydrofuran → Tert-butyl 4-(5-isobutyl-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate

HRID 1045712노트

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HRID 1045712 반응식
Br[C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:4][CH:3]=1.[Br-].[CH2:25]([Zn+])[CH:26]([CH3:28])[CH3:27].C1COCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:25]([C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:4][CH:3]=1)[CH:26]([CH3:28])[CH3:27]

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 58447004Tert-butyl 4-(5-bromo-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylateHCID 178448254HCID 178448254, 화합물

생성물 1

HCID 67393909Tert-butyl 4-(5-isobutyl-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate수율 64%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 1140Toluene용매

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온도
20 °C

실험 절차

A 50 mL round bottom flask was charged with tert-butyl 4-(5-bromo-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate (0.5 g, 1.3 mmol), Pd(PPh3)2Cl2 (140.3 mg, 0.20 mmol) and toluene (8 mL) under N2. To the above was injected a 2 M solution of isobutylzinc(II) bromide in THF (10.4 mL, 5.2 mmol). The resulting mixture was stirred under N2 at 20° C. for 0.5 h then 100° C. overnight. Work-up: the reaction mixture was filtered. The filter cake was washed with EtOAc (10 mL) and the filtrate was extracted with more EtOAc (10 mL×3). The combined organic solutions were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 2% methanol in dichloromethane, to afford 0.30 g (64%) of tert-butyl 4-(5-isobutyl-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate as a yellow solid. MS m/z: 361 (M+H+).

후처리

  1. custom100° C. overnight
  2. filtrationthe reaction mixture was filtered
  3. washThe filter cake was washed with EtOAc (10 mL)
  4. extractionthe filtrate was extracted with more EtOAc (10 mL×3)
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel with 2% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-d8e13b470dc04b8ca00a438668aa6b05
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569300B2

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