Triethylamine → 6-Fluoro-3-((S)-3-triisopropylsilanyloxy-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 1402214노트

반응식

HRID 1402214 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:11]3[CH2:16][CH2:15][CH2:14][C@H:13]([OH:17])[CH2:12]3)=[N:9][N:10]=2)[CH:7]=1.CCN(CC)CC.[CH:25]([Si:28](OS(C(F)(F)F)(=O)=O)([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])([CH3:27])[CH3:26]>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][CH2:14][C@H:13]([O:17][Si:28]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:25]([CH3:27])[CH3:26])[CH2:12]3)=[N:9][N:10]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 86687067HCID 86687067, 화합물

생성물 1

HCID 866870686-Fluoro-3-((S)-3-triisopropylsilanyloxy-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridine수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of Intermediate 63a (204 mg, 0.864 mmol) and Et3N (180 μL, 1.3 mmol) in DCM (5 mL) was added triisopropylsilyltrifluoromethane sulfonate (279 μL, 1.04 mmol) and the mixture stirred at RT for 1 h. The mixture was washed with sat. aq. NaHCO3 solution, dried and concentrated in vacuo. The residue was purified by FCC, using 0-100% EtOAc in cyclohexane, then 10% MeOH in EtOAc, to give the title compound as a pale brown gum (290 mg, 86%). LCMS (Method 3): Rt 4.99 min, m/z 393 [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-5547d2b85df24e3197e52c58b2aff830
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907094B2

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