1,2-Diaminocyclohexane, trans- → N-[4-amino-3-(4-amino-3-methoxyphenyl)thieno[3,2-c]pyridin-7-yl]-2-pyrrolidin-1-ylacetamide triacetate salt

HRID 17231

Reaktionsgleichung

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13]([NH2:18])=[N:14][CH:15]=[C:16](I)[C:11]=3[S:10][CH:9]=2)=[CH:4][C:3]=1[O:19][CH3:20].[N:21]1([CH2:26][C:27]([NH2:29])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22]1.P([O-])([O-])([O-])=[O:31].[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>[Cu]I.O1CCOCC1>[C:3]([OH:19])(=[O:28])[CH3:4].[C:27]([OH:28])(=[O:31])[CH3:26].[C:3]([OH:19])(=[O:28])[CH3:4].[NH2:18][C:13]1[C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([O:19][CH3:20])[CH:4]=3)=[CH:9][S:10][C:11]=2[C:16]([NH:29][C:27](=[O:28])[CH2:26][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][N:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A schlenck tube was charged with 3-(4-amino-3-methoxyphenyl)-7-iodothieno[3,2-c]pyridin-4-amine (199 mg, 0.5 mmol), 2-pyrrolidin-1-ylacetamide (0.6 mmol), copper(I) iodide (4.8 mg, 0.025 mmol), potassium phosphate (225 mg, 1.06 mmol). Evacuated under vacuum and back filled with nitrogen. trans-Cyclohexane-1,2-diamine (6.5 uL, 0.05 mmol) and dioxane (1 mL) was added. The reaction tube was sealed and heated at about 110° C. overnight. The solvent was removed and the crude product was purified by reverse phase preparative HPLC to give the title compound as the tri-acetate salt. LCMS (Conditions a): MH+=398.2, Rt=1.55 min. (154 mg, 45%)

Aufarbeitung

customEvacuated under vacuum
additionback filled with nitrogen
customThe reaction tube was sealed
customThe solvent was removed
customthe crude product was purified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-a1656f847d5b4166abc0cb76fd0c498c
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07737160B2

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