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Hydrochloric Acid → (R)-1-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol

HRID 1523681
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HRID 1523681 반응식
CC1(C)[O:6][C@H:5]([C:7]2[N:11]=[C:10]([NH:12][C:13]3[C:18]([O:19][C:20]4[C:21]([CH3:26])=[N:22][CH:23]=[CH:24][CH:25]=4)=[CH:17][C:16]([S:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[CH:15][N:14]=3)[S:9][N:8]=2)[CH2:4][O:3]1.Cl>C(O)C>[CH3:26][C:21]1[C:20]([O:19][C:18]2[C:13]([NH:12][C:10]3[S:9][N:8]=[C:7]([C@@H:5]([OH:6])[CH2:4][OH:3])[N:11]=3)=[N:14][CH:15]=[C:16]([S:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[CH:17]=2)=[CH:25][CH:24]=[CH:23][N:22]=1
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참가 물질

4

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HCID 313Hydrochloric AcidHCID 68477969(R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-1,2,4-thiadiazol-5-amine

생성물 1

HCID 25235319(R)-1-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol수율 82.4%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

A flask was charged with (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-1,2,4-thiadiazol-5-amine (3.8 g, 7.683 mmol) and added ethanol (40 mL). 3M HCl (5.122 ml, 15.37 mmol) was added, and the reaction was heated to 70° C. for 1 hour, then cooled to ambient temperature. The ethanol removed in vacuo and saturated sodium bicarbonate solution was added. The aqueous layer was extracted with ethyl acetate. The majority of product crashed out of the aqueous layer and collected by filtration. The solids and residue from organic layer were purified over silica gel (10-15% methanol in ethyl acetate) to afford (R)-1-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol (2.877 g, 6.330 mmol, 82.38% yield) as yellow solid. Mass Spectrum (apci) m/z=455.1 (M+H).

후처리

  1. temperaturecooled to ambient temperature
  2. customThe ethanol removed in vacuo and saturated sodium bicarbonate solution
  3. additionwas added
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. filtrationcollected by filtration
  6. customThe solids and residue from organic layer were purified over silica gel (10-15% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-248d7209a1fa4acc86133f02467312a2
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079890B2

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