Hydrochloric Acid → Methyl 6-[1-(6-cyanopyridin-3-yl)-1H-pyrazol-5-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate

HRID 1958302노트

반응식

HRID 1958302 반응식
C(O[CH:4](OCC)[C:5]#[C:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10](=[O:17])[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:8]=1[CH3:28])C.FC(F)(F)C(O)=O.[NH:39]([C:41]1[CH:42]=[CH:43][C:44]([C:47]#[N:48])=[N:45][CH:46]=1)[NH2:40].Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[C:47]([C:44]1[N:45]=[CH:46][C:41]([N:39]2[C:6]([C:7]3[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10](=[O:17])[N:9]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[CH:19]=4)[C:8]=3[CH3:28])=[CH:5][CH:4]=[N:40]2)=[CH:42][CH:43]=1)#[N:48]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59564940Methyl 6-(3,3-diethoxyprop-1-ynyl)-5-methyl-3-oxo-4-(3-(trifluoromethyl)phenyl)-3,4-dihydropyrazine-2-carboxylateHCID 667386805-Hydrazinopyridine-2-carbonitrile trifluoroacetate

생성물 1

HCID 66738829Methyl 6-[1-(6-cyanopyridin-3-yl)-1H-pyrazol-5-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate수율 28.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
55 °C

실험 절차

Methyl 6-(3,3-diethoxyprop-1-ynyl)-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (0.073 g, 0.17 mmol) and 5-hydrazinopyridine-2-carbonitrile trifluoroacetate (0.050 g, 0.20 mmol) in dioxane (3 ml) were placed in a vial. 2M HCl (0.188 ml) was added and the mixture was stirred at 55° C. for 15 min. After cooling, NaHCO3 (0.048 g) was added and the mixture was extracted with DCM and water. The combined organic phases were washed with water, brine, dried (Na2SO4) and evaporated. The residue was dissolved in acetic acid (10 ml) and the vial was sealed. The solution was stirred at 90° C. for 10 h. After evaporation, the residue was purified by preparative HPLC to give 0.023 g (28%) of the title compound.

후처리

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with DCM and water
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in acetic acid (10 ml)
  7. customthe vial was sealed
  8. stirringThe solution was stirred at 90° C. for 10 h
  9. customAfter evaporation
  10. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-7b497569e14b4b669cdadb8398274017
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410114B2

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