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

HRID 1511126노트

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HRID 1511126 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:9]=[C:10]([O:30][C:31]2[C:32]([CH3:38])=[N:33][N:34]([CH3:37])[C:35]=2[CH3:36])[C:11]([NH:14][C:15]2[S:19][N:18]=[C:17]([C@H:20]3[CH2:24][O:23]C4(CCCCC4)[O:21]3)[N:16]=2)=[N:12][CH:13]=1.[ClH:39].C(=O)(O)[O-].[Na+]>C(O)C>[ClH:39].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:9]=[C:10]([O:30][C:31]2[C:32]([CH3:38])=[N:33][N:34]([CH3:37])[C:35]=2[CH3:36])[C:11]([NH:14][C:15]2[S:19][N:18]=[C:17]([C@H:20]([OH:21])[CH2:24][OH:23])[N:16]=2)=[N:12][CH:13]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67487345(S)-N-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decane-2-yl)-1,2,4-thiadiazol-5-amine

생성물 1

HCID 67486348(S)-1-(5-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol hydrochloride수율 66%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
75 °C

실험 절차

A flask was charged with (S)-N-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine (1.38 g, 2.50 mmol), ethanol (50 mL), and 3M HCl (1.67 ml, 5.00 mmol) and heated to 75° C. for 1 hour. The reaction was cooled to ambient temperature, and saturated aqueous sodium bicarbonate was added slowly. The mixture was extracted with ethyl acetate and dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified over silica gel (50 to 100% ethyl acetate in hexanes followed 5% methanol in ethyl acetate). The product was dissolved in 10% methanol in dichloromethane and 5 mL 2M HCl in ether was added. The solution was concentrated and dried in a vacuum oven to afford (S)-1-(5-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol hydrochloride (0.958 g, 1.65 mmol, 65.9% yield) as yellow solid. Mass Spectrum (apci) m/z=472.1 (M+H—HCl).

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate and dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified over silica gel (50 to 100% ethyl acetate in hexanes followed 5% methanol in ethyl acetate)
  7. dissolutionThe product was dissolved in 10% methanol in dichloromethane
  8. addition5 mL 2M HCl in ether was added
  9. concentrationThe solution was concentrated
  10. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-74df0c2568c04a878389a6c226245fab
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212045B2

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