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Dimethylformamide → 4-[3-((2S,6R)-2,6-Dimethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-cyclohexylamine

HRID 2200046
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2200046
[H-].[Na+].[NH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([OH:10])[CH2:6][CH2:5]1.F[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:27])=[N:19][N:20]=2)[CH:17]=1.[CH3:28]N(C=O)C>>[CH3:27][C@H:22]1[CH2:23][CH2:24][CH2:25][C@@H:26]([CH3:28])[N:21]1[C:18]1[N:16]2[CH:17]=[C:12]([O:10][CH:7]3[CH2:8][CH2:9][CH:4]([NH2:3])[CH2:5][CH2:6]3)[CH:13]=[CH:14][C:15]2=[N:20][N:19]=1
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Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 866871056-Fluoro-3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridineHCID 178511715HCID 178511715, Verbindung

Produkt 1

HCID 1177290354-[3-((2S,6R)-2,6-Dimethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-cyclohexylamineAusbeute 27 %

Versuchsvorschrift

Sodium hydride (60% in mineral oil, 0.26 g, 6.39 mmol) was added to a stirred solution of trans-4-amino cyclohexanol (0.397 g, 3.45 mmol) in anhydrous DMF (10 mL) at RT under an argon atmosphere. The reaction mixture was stirred at RT for 30 min, then Intermediate 2d (0.50 g, 2.13 mmol) in anhydrous DMF (4 mL) was added and stirred at 60° C. for 10 h. After cooling, the reaction mixture was quenched by careful addition of a saturated aqueous solution of NH4Cl and water (1:1) and extracted with EtOAc and then DCM. The combined organic extracts were concentrated in vacuo and the resultant residue was purified by FCC, using 0-25% [2M NH3 in MeOH] in DCM, to afford the title compound (0.193 g, 27%) as an orange residue. LCMS (Method 3): Rt 2.00 min, m/z 330 [MH+].

Aufarbeitung

  1. stirringstirred at 60° C. for 10 h
  2. temperatureAfter cooling
  3. customthe reaction mixture was quenched by careful addition of a saturated aqueous solution of NH4Cl and water (1:1)
  4. extractionextracted with EtOAc
  5. concentrationThe combined organic extracts were concentrated in vacuo
  6. customthe resultant residue was purified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-2b30c960f306467ebcbbe8bf7635586b
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09359354B2

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