Hydrochloric Acid → HCID 178513766, 화합물

HRID 521205노트

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HRID 521205 반응식
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:12]([C:13]#[N:14])=[CH:11][N:10](COCC[Si](C)(C)C)[N:9]=2)=[CH:3][CH:2]=1.N1C=CC(NC2N(C[O:36]CC[Si](C)(C)C)N=CC=2C#N)=CC=1.[OH-].[Na+].OO.Cl>CS(C)=O.CCO.CO>[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:12]([C:13]([NH2:14])=[O:36])=[CH:11][NH:10][N:9]=2)=[CH:3][CH:2]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric Acid2회HCID 784Hydrogen Peroxide2회HCID 14798Sodium Hydroxide2회HCID 86729366HCID 86729366, 화합물HCID 86729367HCID 86729367, 화합물

생성물 1

HCID 178513766HCID 178513766, 화합물

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 702Ethanol용매HCID 887Methanol용매

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온도
55 °C

실험 절차

To a solution containing a mixture of 3-(pyridin-4-ylamino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carbonitrile and 5-(pyridin-4-ylamino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carbonitrile (150 mg, 0.5 mmol) in DMSO (1.2 mL) and EtOH (1.2 mL) was added 5M aqueous NaOH (0.7 mL, 3.3 mmol). The mixture was heated to 55° C., followed by the dropwise addition of 30% H2O2 (0.7 mL, 7.1 mmol). After 10 minutes, additional 30% H2O2 (0.30 mL, 3.4 mmol) was added dropwise. The mixture was maintained for 30 minutes before it was allowed to cool to ambient temperature. To the crude reaction mixture was added MeOH (1 mL) and 6N aqueous HCl (2 mL). The resulting mixture was heated at 55° C. for 1.5 hours. Additional 6N aqueous HCl (1 mL) was added and the mixture continued stirring for another 1 hour. The mixture was cooled to ambient temperature and carefully neutralized with 5N aqueous NaOH until pH 6-7. The mixture was then concentrated in vacuo to remove most of the solvent. To the slurry-like residue was added MeOH (20 mL), and the resulting mixture was sonicated for 5 minutes. The mixture was filtered to remove insoluble precipitate and the filtrate was concentrated in vacuo to afford crude residue containing the title compound, Intermediate #34-1, which was used without further purification.

후처리

  1. additionTo a solution containing
  2. temperatureThe mixture was maintained for 30 minutes before it
  3. temperatureto cool to ambient temperature
  4. customTo the crude reaction mixture
  5. temperatureThe resulting mixture was heated at 55° C. for 1.5 hours
  6. temperatureThe mixture was cooled to ambient temperature
  7. concentrationThe mixture was then concentrated in vacuo
  8. customto remove most of the solvent
  9. additionTo the slurry-like residue was added MeOH (20 mL)
  10. customthe resulting mixture was sonicated for 5 minutes
  11. filtrationThe mixture was filtered
  12. customto remove insoluble precipitate
  13. concentrationthe filtrate was concentrated in vacuo
  14. customto afford crude residue

출처 및 근거

ORD 기록
ord-960bac59cbb14fd6b878bf1db180ee08
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328099B2

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