Toluene → HCID 178489801, 화합물

HRID 1092080

반응식

HRID 1092080 반응식
C[Al](C)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]([NH2:22])[NH:20][N:21]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.Cl[C:24]1[N:25]=[CH:26][C:27]([C:30]([O:32]C)=O)=[N:28][CH:29]=1.[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36]C=1>>[CH2:40]1[CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][N:28]2[CH2:29][CH2:24][N:25]1[C:24]1[N:25]=[CH:26][C:27]([C:30]([NH:22][C:19]2[NH:20][N:21]=[C:17]([CH2:16][CH2:15][C:9]3[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=3)[CH:18]=2)=[O:32])=[N:28][CH:29]=1

참가 물질

5

반응물 4

HCID 1140TolueneHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 16682925TrimethylaluminumHCID 178489815HCID 178489815, 화합물

생성물 1

HCID 178489801HCID 178489801, 화합물수율 63%

실험 절차

Trimethylaluminium (2M in toluene, 9.64 ml, 19.28 mmol) was added dropwise to a stirred suspension of 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (1.91 g, 7.71 mmol) and methyl 5-chloropyrazine-2-carboxylate (1.33 g, 7.71 mmol) in anhydrous toluene (38.6 ml) at ambient temperature. The resulting solution was then stirred under nitrogen at ambient temperature for 18 h. The reaction was incomplete so the temperature was increased to 60° C. and the reaction mixture was stirred for a further 3 h. The reaction mixture was quenched with methanol (10 mL) and HCl (2M aqueous solution). The mixture was diluted with EtOAc (100 mL) and water (250 mL) and then acidified with HCl (2N aqueous solution). The organic layer was removed and the aqueous further extracted with EtOAc (2×100 mL). The combined organics were washed with water (200 mL), brine (200 mL) dried over MgSO4 and concentrated under reduced pressure. Upon concentration a precipitate formed. The precipitate was collected by filtration, washed with MeOH (10 mL) and air dried to afford the desired compound (1.88 g, 63%) as a yellow solid, which was used without further purification.

후처리

  1. temperaturewas increased to 60° C.
  2. stirringthe reaction mixture was stirred for a further 3 h
  3. customThe reaction mixture was quenched with methanol (10 mL) and HCl (2M aqueous solution)
  4. additionThe mixture was diluted with EtOAc (100 mL) and water (250 mL)
  5. customThe organic layer was removed
  6. extractionthe aqueous further extracted with EtOAc (2×100 mL)
  7. washThe combined organics were washed with water (200 mL), brine (200 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. concentrationUpon concentration a precipitate
  11. customformed
  12. filtrationThe precipitate was collected by filtration
  13. washwashed with MeOH (10 mL) and air
  14. customdried

출처 및 근거

ORD 기록
ord-a50b1412f71d407a99745ed00a378867
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129391B2

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