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Ethanol → N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amine

HRID 1621413
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HRID 1621413 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]2[C:23]([C:24]3[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([S:31][CH3:32])[N:25]=3)=[CH:22][C:19]([CH:20]=O)=[CH:18][N:17]=2)=[CH:11][CH:10]=1.CCO.C([BH3-])#N.[Na+]>CC(O)=O.O.CCOC(C)=O>[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]2[C:23]([C:24]3[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([S:31][CH3:32])[N:25]=3)=[CH:22][C:19]([CH2:20][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:18][N:17]=2)=[CH:11][CH:10]=1
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참가 물질

8

반응물 4

HCID 702EthanolHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 866470496-(6-Methoxypyridin-3-ylamino)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)nicotinaldehyde

생성물 1

HCID 66612061N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amine수율 63.7%

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Morpholine (0.018 mL, 0.204 mmol) and a few drops of AcOH (3.88 μL, 0.068 mmol) were added to a stirred suspension of 6-(6-methoxypyridin-3-ylamino)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)nicotinaldehyde (25 mg, 0.068 mmol) in EtOH (3.00 mL, 51.4 mmol), the mixture was stirred at room temperature for 1 h, then treated with sodium cyanoborohydride (4.26 mg, 0.068 mmol) and stirred at room temperature overnight. The mixture was diluted with water and EtOAc (10 mL each). The separated aqueous layer was extracted with ethyl acetate (2×10 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude product which was purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., DCM to 10% DCM in MeOH) to give N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amine (19 mg, 0.043 mmol, 63.7% yield) as a yellow solid. LCMS (API-ES) m/z 440 (M+H)+.

후처리

  1. stirringstirred at room temperature overnight
  2. extractionThe separated aqueous layer was extracted with ethyl acetate (2×10 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product which
  7. customwas purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., DCM to 10% DCM in MeOH)

출처 및 근거

ORD 기록
ord-7480d9e94a094933bc9a8462f6fa5815
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772480B2

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