Hydrochloric Acid → (S)-1-(5-(3-(1-ethyl-1H-pyrazol-5-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol

HRID 534041노트

반응식

HRID 534041 반응식
[CH2:1]([N:3]1[C:7]([O:8][C:9]2[C:10]([NH:22][C:23]3[S:27][N:26]=[C:25]([C@H:28]4[CH2:32][O:31]C5(CCCCC5)[O:29]4)[N:24]=3)=[N:11][CH:12]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:14]=2)=[CH:6][CH:5]=[N:4]1)[CH3:2].O.Cl>CCO>[CH2:1]([N:3]1[C:7]([O:8][C:9]2[C:10]([NH:22][C:23]3[S:27][N:26]=[C:25]([C@H:28]([OH:29])[CH2:32][OH:31])[N:24]=3)=[N:11][CH:12]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:14]=2)=[CH:6][CH:5]=[N:4]1)[CH3:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68472914(S)-N-(3-(1-ethyl-1H-pyrazol-5-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine

생성물 1

HCID 25210589(S)-1-(5-(3-(1-ethyl-1H-pyrazol-5-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a mixture of (S)-N-(3-(1-ethyl-1H-pyrazol-5-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decane-2-yl)-1,2,4-thiadiazol-5-amine (1.24 g, 2.31 mmol) in EtOH (25 ml) and H2O (1.09 ml, 2.31 mmol) was added concentrated HCl (0.480 ml, 5.77 mmol) and the reaction was heated at reflux for 8 hours. The reaction was allowed to cool to ambient temperature and stirred overnight. The mixture was concentrated to a residue that was dissolved in EtOAc and saturated aqueous NaHCO3. The combined organic layers were washed with water, dried over NaSO4, filtered and concentrated. The residue was purified over silica gel (3% MeOH/CH2Cl2) to afford (S)-1-(5-(3-(1-ethyl-1H-pyrazol-5-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol as cream solids. The solids were dissolved in CH2Cl2 (25 ml) and 1N HCl in Et2O (20 ml) was added. The mixture was concentrated to dryness and dried in the vacuum oven to afford (S)-1-(5-(3-(1-ethyl-1H-pyrazol-5-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol hydrochloride (0.569 g, 49.9% yield) as air off-white solid. Mass spectrum (apci) m/z=458.1 (M+H−HCl).

후처리

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 8 hours
  3. concentrationThe mixture was concentrated to a residue that
  4. dissolutionwas dissolved in EtOAc
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified over silica gel (3% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-291f3e71cb6a4c71a93444a47a0a10e8
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853409B2

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