1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-{[7-Cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carbonyl]amino}-2-cyclopropyl-propionic acid tert-butyl ester

HRID 1481229Notizen

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:13])[CH:7]([CH:10]1[CH2:12][CH2:11]1)[CH2:8][NH2:9])([CH3:4])([CH3:3])[CH3:2].C(O[C:17]([C:19]1[N:20]=[C:21](C#N)[C:22]2[C:27]([C:28]=1[OH:29])=[CH:26][CH:25]=[C:24]([O:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)[CH:23]=2)=[O:18])C.C1CCN2[C:42](=[N:43]CCC2)CC1>CC(N(C)C)=O>[C:1]([O:5][C:6](=[O:13])[CH:7]([CH:10]1[CH2:12][CH2:11]1)[CH2:8][NH:9][C:17]([C:19]1[N:20]=[CH:21][C:22]2[C:27]([C:28]=1[OH:29])=[CH:26][CH2:25][C:24]([C:42]#[N:43])([O:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)[CH:23]=2)=[O:18])([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A mixture of 3-amino-2-cyclopropyl-propionic acid tert-butyl ester (39 mg), 1-cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester (28 mg) and DBU (0.019 mL) in DMA (0.5 mL) was heated in an oil bath (150° C.) for 1 h. The reaction mixture was then partitioned between EtOAc and diluted HCl solution, EtOAc phase was separated and washed with water, diluted NaCl solution and dried over anhydrous sodium sulfate solution, filtered, concentrated and silica gel column purified to give desired product (21 mg). LC-MS ESI+: 475 (M+1)+.

Aufarbeitung

customThe reaction mixture was then partitioned between EtOAc and diluted HCl solution, EtOAc phase
customwas separated
washwashed with water, diluted NaCl solution
dry with materialdried over anhydrous sodium sulfate solution
filtrationfiltered
concentrationconcentrated
customsilica gel column purified

Quellen und Nachweise

ORD-Eintrag: ord-6f0f02f28d1d4b9aa97333ebb94001e3
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09409892B2

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