HCID 58345904, Verbindung → HCID 58553169, Verbindung

HRID 1046528

Reaktionsgleichung

CS([C:4]1[N:9]=[C:8]([C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([OH:22])([CH3:21])[CH3:20])[C:13]3=[N:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1)=O.[CH3:23][S:24]([CH2:27][CH:28]1[CH2:33][CH2:32][CH:31]([NH2:34])[CH2:30][CH2:29]1)(=[O:26])=[O:25]>CN1C(=O)CCC1.O>[CH3:23][S:24]([CH2:27][CH:28]1[CH2:33][CH2:32][CH:31]([NH:34][C:4]2[N:9]=[C:8]([C:10]3[N:14]4[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([OH:22])([CH3:20])[CH3:21])[C:13]4=[N:12][CH:11]=3)[CH:7]=[CH:6][N:5]=2)[CH2:30][CH2:29]1)(=[O:25])=[O:26]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 2-[3-(2-methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol (75 mg), 4-methanesulfonylmethyl-cyclohexylamine (162 mg), and TEA (0.165 mL) in NMP (2 mL) was stirred at 100° C. overnight. The reaction mixture was then cooled to RT, and diluted with water. The resulting precipitate was filtered and dried, then purified by ISCO using 100% DCM to 10% MeOH/DCM. The fractions were collected, concentrated, and titurated with EtOAc. The resulting solid was filtered and dried at 50° C. under vacuum overnight to provide 2-{3-[2-(4-methanesulfonylmethyl-cyclohexylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyridin-8-yl}-propan-2-ol (Compound 1, 55.5 mg). Mp=223-224° C.

Aufarbeitung

temperatureThe reaction mixture was then cooled to RT
filtrationThe resulting precipitate was filtered
customdried
custompurified by ISCO
customThe fractions were collected
concentrationconcentrated
filtrationThe resulting solid was filtered
customdried at 50° C. under vacuum overnight

Quellen und Nachweise

ORD-Eintrag: ord-8172da2e90f4453281532ffa792a72a2
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08569306B2

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