1,8-Diazabicyclo(5.4.0)undec-7-ene → (1S,3R,4R)-methyl 3-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)-4-hydroxycyclopentanecarboxylate

HRID 56388

Reaktionsgleichung

Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[C:17]([Cl:18])=[C:16]([O:19][CH3:20])[CH:15]=[C:14]([O:21][CH3:22])[C:13]=3[Cl:23])[CH:8]=2)[N:3]=1.[NH2:24][C@H:25]1[C@H:29]([OH:30])[CH2:28][CH:27]([C:31]([O:33][CH3:34])=[O:32])[CH2:26]1.C1CCN2C(=NCCC2)CC1>C(#N)C.CCOC(C)=O>[Cl:18][C:17]1[C:16]([O:19][CH3:20])=[CH:15][C:14]([O:21][CH3:22])=[C:13]([Cl:23])[C:12]=1[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:24][C@H:25]1[C@H:29]([OH:30])[CH2:28][C@@H:27]([C:31]([O:33][CH3:34])=[O:32])[CH2:26]1)[N:11]=[CH:10]2

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline (0.576 g, 1.558 mmol), methyl (3R,4R)-3-amino-4-hydroxycyclopentane-1-carboxylate (0.372 g, 2.337 mmol) were taken up in acetonitrile (3 ml) and DBU (0.470 ml, 3.12 mmol) was added. The reaction was purged with N2 for 5 minutes then heated to 65° C. overnight. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was purified via flash chromatography (0-100% Hex/EtOAc; 12 g column), and (1S,3R,4R)-methyl 3-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)-4-hydroxycyclopentanecarboxylate (0.520 g, 1.056 mmol, 67.8% yield) was recovered. MS (ES+) C23H23Cl2N3O5 requires: 492, found: 493 [M+H]+.

Aufarbeitung

customThe reaction was purged with N2 for 5 minutes
temperatureAfter cooling to room temperature
customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-18577f484c0a489aa3234c21a76ea822
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09434700B2

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