7,12-Dimethylbenz(a)anthracene → 6-(3-amino-2-fluoropropyl)-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one

HRID 1783763

Reaktionsgleichung

C([NH:4][CH2:5][CH:6]([F:23])[CH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11]2=[N:19][NH:20][C:21](=[O:22])[N:10]2[CH:9]=1)C=C.CC1C2C(=CC=CC=2)C(C)=C2C=1C=CC1C2=CC=CC=1>C(Cl)CCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:4][CH2:5][CH:6]([F:23])[CH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11]2=[N:19][NH:20][C:21](=[O:22])[N:10]2[CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

6-[3-(allylamino)-2-fluoropropyl]-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (6-4)(18 mg, 0.054 mmol, 1.0 equiv) and DMBA (25.2 mg, 0.16 mmol, 3.0equiv) and tetrakis(triphenylphosphine)palladium(0) (3 mg, 2.60 μmol, 0.05 equiv) were suspended in ClCH2CH2Cl (1 mL). The resulted yellow suspension was heated at 50° C. LCMS at 5 hours showed mostly product. The crude was purified with reverse phase HPLC H2O/CH3CN gradient w/0.1% TFA present) to afford the pure product (6-5). 1H NMR (500 MHz, CD3OD) δ 8.26 (d, 1H, J=2.3 Hz), 7.88 (d, 1H, J=8.5 Hz), 7.72 (dd, 1H, J=8.5, 2.3 Hz), 7.61 (s, 1H), 5.19-4.94 (dm, 1H, J=50.0 Hz), 3.52-3.33 (m, ˜4H, overlap w/solvent peak). LRMS m/z (M+H) 295.3 found, 295.1 required.

Aufarbeitung

customThe crude was purified with reverse phase HPLC H2O/CH3CN gradient w/0.1% TFA present)

Quellen und Nachweise

ORD-Eintrag: ord-2926e3e4600e447a87afe72415ea8a63
Quelldatensatz: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07501435B2

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