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Triethylamine → 6-Fluoro-3-(4-triisopropylsilanyloxyethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin

HRID 2285047
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HRID 2285047 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:11]3[CH2:16][CH2:15][CH:14]([CH:17](O)[CH3:18])[CH2:13][CH2:12]3)=[N:9][N:10]=2)[CH:7]=1.CCN(CC)CC.[CH:27]([Si:30]([O:37]S(C(F)(F)F)(=O)=O)([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])([CH3:29])[CH3:28]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:11]3[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][O:37][Si:30]([CH:31]([CH3:33])[CH3:32])([CH:34]([CH3:36])[CH3:35])[CH:27]([CH3:28])[CH3:29])[CH2:13][CH2:12]3)=[N:9][N:10]=2)[CH:7]=1
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참가 물질

5

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HCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 86687072[1-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-piperidin-4-yl]-ethanol

생성물 1

HCID 866870716-Fluoro-3-(4-triisopropylsilanyloxyethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

To a solution of Intermediate 66a (319 mg, 1.21 mmol) and Et3N (252 μL, 1.82 mmol) in DCM (10 mL) was added triisopropylsilyltrifluoromethane sulfonate (319 μL, 1.45 mmol) and the mixture stirred at RT for 1.5 h. The mixture was washed with sat. aq. NaHCO3 solution, dried and concentrated in vacuo. The residue was purified by FCC, using 0-10% MeOH in DCM, to give the title compound as an orange solid (465 mg, 92%). LCMS (Method 3): Rt 5.35 min, m/z 421 [MH+].

후처리

  1. washThe mixture was washed with sat. aq. NaHCO3 solution
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC

출처 및 근거

ORD 기록
ord-d554655bb5c84d268745ef403e37445e
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09145413B2

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