Diisopropylethylamine → (+/-) N-(3-{[2-(12,12-Dioxo-12lambda6-thia-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-4-ylamino)-5-trifluoromethyl-pyrimidin-4-ylamino]-methyl}-pyridin-2-yl)-N-methyl-methanesulfonamide

HRID 1161645

Reaktionsgleichung

Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:23]=[CH:22][C:21]3[CH:20]4[S:24](=[O:26])(=[O:25])[CH:16]([CH2:17][CH2:18][CH2:19]4)[C:15]=3[CH:14]=2)[N:3]=1.[NH2:27][CH2:28][C:29]1[C:30]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[N:31][CH:32]=[CH:33][CH:34]=1.C(N(C(C)C)CC)(C)C>CC(O)(C)C.ClC(Cl)C>[O:25]=[S:24]1(=[O:26])[CH:20]2[CH2:19][CH2:18][CH2:17][CH:16]1[C:15]1[CH:14]=[C:13]([NH:12][C:4]3[N:3]=[C:2]([NH:27][CH2:28][C:29]4[C:30]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[N:31][CH:32]=[CH:33][CH:34]=4)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=3)[CH:23]=[CH:22][C:21]=12

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

A mixture of C6 (51 mg; 0.126 mmol) and 1:1 (vol:vol) t-BuOH/dichloroethane (500 μL) was added to a mixture of N-(3-Aminomethyl-pyridin-2-yl)-N-methyl-methanesulfonamide (38 mg, 0.139 mmol) and diisopropyl ethylamine (66 μL, 0.378 mmol). The reaction mixture was heated to 85° C. in a sealed vial. After two hours, the hot reaction mixture was loaded directly onto silica under reduced pressure, purified via chromatography (99:1:0.1 CHCl3:CH3OH:NH4OH), and concentrated under reduced pressure to provide 1 as a white solid (13 mg, 0.0223 mmol, 18%). LC/MS (Method F) r.t.=2.26 min.; m/z 583.2. HPLC r.t.=6.40 min.

Aufarbeitung

custompurified via chromatography (99:1:0.1 CHCl3:CH3OH:NH4OH)
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-98a7861602504b46a4637384b2933871
Quelldatensatz: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07820648B2

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