Cesium carbonate → 2-({3-[1-(cyclohexylamino)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}oxy)acetamide

HRID 601289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601289
[CH:1]1([NH:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([OH:18])=[C:10]([C:19]3[NH:24][C:23]4[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:22]=4[S:21](=[O:31])(=[O:30])[N:20]=3)[C:9]2=[O:32])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:40][C:41]([NH2:43])=[O:42]>CN(C)C=O>[CH:1]1([NH:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([OH:18])=[C:10]([C:19]3[NH:24][C:23]4[CH:25]=[CH:26][C:27]([O:29][CH2:40][C:41]([NH2:43])=[O:42])=[CH:28][C:22]=4[S:21](=[O:30])(=[O:31])[N:20]=3)[C:9]2=[O:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 1363742711-(cyclohexylamino)-4-hydroxy-3-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)quinolin-2(1H)-one

Produkt 1

HCID 1363737832-({3-[1-(cyclohexylamino)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}oxy)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product of Example 306C (13 mg, 0.028 mmol) in N,N-dimethylformamide (5 mL) was reacted with cesium carbonate (0.0137 g, 0.114 mol) and 2-bromoacetamide (0.008 g, 0.058 mmol) according to the procedure as described in Example 304J to give the title compound. The sodium salt was prepared according to the procedure of Example 1D (7 mg, 48%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.36 (m, 10 H) 2.96 (bs, 1 H) 4.49 (s, 2 H) 5.67 (d, J=4.04 Hz, 1 H) 7.04 (t, J=7.54 Hz, 1 H) 7.20 (m, 3 H) 7.40 (s, 1 H) 7.47 (m, 1 H) 7.62 (s, 1 H) 7.74 (d, J=8.46 Hz, 1 H) 8.05 (d, J=6.62 Hz, 1 H) 16.26 (s, 1 H). (ESI−) m/z 510 (M−H)−, m/z 532 (M+Na−H)−1.

Quellen und Nachweise

ORD-Eintrag
ord-e176511cb65e48b290d9a84f2de00f50
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902203B2

Notizen zur Reaktion

Wird geladen…