Ammonium Hydroxide → 2-(4-(4-((6-Aminopyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

HRID 1972534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972534
Cl[C:2]1[N:7]=[N:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[NH4+:34]>CCO>[NH2:34][C:2]1[N:7]=[N:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 569326312-(4-(4-((6-Chloropyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

Produkt 1

HCID 866703892-(4-(4-((6-Aminopyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanolAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a 2 mL microwave vial was added 2-(4-(4-((6-chloropyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (50 mg, 0.099 mmol), EtOH (1.0 mL) and ammonium hydroxide (2.0 mL, 51 mmol). The solution was heated in an Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 110° C. for 1 h and then concentrated. The resulting material was purified by silica gel chromatography (0 to 4% MeOH in CH2Cl2) to afford 2-(4-(4-((6-aminopyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (29 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (s, 1H), 7.67 (d, J=9.4 Hz, 1H), 7.47 (d, J=8.6 Hz, 2H), 7.28 (s, 2H), 7.02 (d, J=9.0 Hz, 2H), 6.89 (d, J=9.2 Hz, 1H), 3.29-3.33 (m, 4H), 3.22-3.28 (m, 4H). m/z (ESI, +ve ion) 485.9 (M+H)+. GK-GKRP IC50 (Binding)=0.285 μM; GK-GKRP EC50 (LC MS/MS-2)=0.302 μM.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe resulting material was purified by silica gel chromatography (0 to 4% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-ff912096557048a493589630f3deaf5d
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431563B2

Notizen zur Reaktion

Wird geladen…