Carbon Dioxide → HCID 54548042, Verbindung

HRID 1954786

Reaktionsgleichung

[C:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:7][CH:8]=1)([OH:3])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[NH2:30][C@@H:31]1[CH2:40][CH2:39][C:38]2[C:33](=[C:34]([N:41]3[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]3)[CH:35]=[CH:36][CH:37]=2)[CH2:32]1>CN(C)C=O>[CH3:47][N:44]1[CH2:45][CH2:46][N:41]([C:34]2[CH:35]=[CH:36][CH:37]=[C:38]3[C:33]=2[CH2:32][C@H:31]([NH:30][C:1]([C:4]2[N:5]=[C:6]([C:9]4[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=4)[S:7][CH:8]=2)=[O:3])[CH2:40][CH2:39]3)[CH2:42][CH2:43]1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

To a solution of 4-carboxy-2-(4-pyridyl)thiazole (89 mg, 0.43 mmol) in anhydrous N,N-dimethylformamide (25 mL) was added 1,1'-carbonyldiimidazole (73 mg, 0.45 mmol) and the reaction was heated at 75° C. When the carbon dioxide evolution had ceased (after 30 min), the reaction was cooled to room temperature and a solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (100 mg, 0.41 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added. The reaction was allowed to stir at ambient temperature for 17 h and the solvent was evaporated in vacuo. Purification on a silica gel column using chloroform/ethanol saturated with NH3 (100:3) as the eluent gave 110 mg (61% yield) of the title compound as white crystals: mp 187-188° C.; [α]21D -82° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 433 (2, M+).

Aufarbeitung

custom(after 30 min)
temperaturethe reaction was cooled to room temperature
customthe solvent was evaporated in vacuo
customPurification on a silica gel column

Quellen und Nachweise

ORD-Eintrag: ord-41a6c749f9204580a6b4a104fd2aa38e
Quelldatensatz: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06124283

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