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Triethylamine → 2-(4-{4-[(6-Aminopyridin-3-Yl)sulfonyl]piperazin-1-Yl}phenyl)-1,1,1,3,3,3-Hexafluoropropan-2-Ol

HRID 1972465
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1972465
Cl.Cl.[F:3][C:4]([F:24])([F:23])[C:5]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)([OH:10])[C:6]([F:9])([F:8])[F:7].C([N:27](CC)CC)C.Cl[C:33]1[N:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1.[OH-].[NH4+]>O.CCOC(C)=O.CCO.C(Cl)Cl>[NH2:27][C:33]1[N:38]=[CH:37][C:36]([S:39]([N:20]2[CH2:21][CH2:22][N:17]([C:14]3[CH:13]=[CH:12][C:11]([C:5]([OH:10])([C:6]([F:9])([F:8])[F:7])[C:4]([F:3])([F:23])[F:24])=[CH:16][CH:15]=3)[CH2:18][CH2:19]2)(=[O:41])=[O:40])=[CH:35][CH:34]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 866703461,1,1,3,3,3-Hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride

Produkt 1

HCID 736591502-(4-{4-[(6-Aminopyridin-3-Yl)sulfonyl]piperazin-1-Yl}phenyl)-1,1,1,3,3,3-Hexafluoropropan-2-Ol

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 250-mL round-bottomed flask was charged with 1,1,1,3,3,3-hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol dihydrochloride (2.50 g, 6.23 mmol), 20 mL of CH2Cl2, triethylamine (3.47 mL, 24.93 mmol), and 6-chloropyridine-3-sulfonyl chloride (1.32 g, 6.23 mmol, Organic Process Research & Development 2009, 13, 875). After stirring at room temperature for 30 min, water was added and the layers were separated. The organics were dried (MgSO4), filtered, and concentrated to give an oily solid. To this material was added 10 mL of EtOH and concentrated ammonium hydroxide (9.95 mL, 255 mmol). The vessel was sealed and heated at 120° C. for 12 h. After the mixture was allows to cool to room temperature, EtOAc (100 mL) and water (50 mL) were added. The organics were separated, dried (MgSO4), filtered and concentrated to give an oil. Purification via column chromatography on silica gel (0 to 70% EtOAc in hexanes) delivered 2-(4-(4-((6-amino-3-pyridinyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (1.65 g) as an off-white solid. 1H NMR (400 MHz, CD3OD) δ=8.30 (d, J=2.3 Hz, 1H), 7.74 (dd, J=2.4, 8.9 Hz, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.00 (d, J=9.0 Hz, 2H), 6.64 (d, J=8.8 Hz, 1H), 3.35-3.30 (m, 4H), 3.17-3.11 (m, 4H). m/z (ESI, +ve ion) 484.9 (M+H)+. GK-GKRP IC50 (Binding)=0.085 μM; GK-GKRP EC50 (LC MS/MS-2)=0.142 μM.

Aufarbeitung

  1. customthe layers were separated
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an oily solid
  6. customThe vessel was sealed
  7. temperatureheated at 120° C. for 12 h
  8. temperatureto cool to room temperature
  9. customThe organics were separated
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto give an oil
  14. customPurification via column chromatography on silica gel (0 to 70% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-548e8fb16b294425998d8bd2abfc8dea
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08431563B2

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