Sodium Bicarbonate → (3R,1R)-8-(3-(1-Aminoethyl)pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride

HRID 1450082

Reaktionsgleichung

Reaktionsgleichung von HRID 1450082
C(OC(C1C(=O)[N:14]2C(C(C)=C([Cl:18])[C:12](F)=[CH:13]2)=C(C2CC2)C=1)=O)C.C(=O)(O)[O-].[Na+].Cl.CN(C)[C@@H:31]1[CH2:35][CH2:34][N:33]([C:36]2[C:37]([F:54])=[CH:38][N:39]3[C:44]([C:45]=2[CH3:46])=[C:43]([CH:47]2[CH2:49][CH2:48]2)[CH:42]=[C:41]([C:50]([OH:52])=[O:51])[C:40]3=[O:53])[CH2:32]1.C(OC(NC(N1CCCC1)C)=O)(C)(C)C>C(#N)C>[ClH:18].[NH2:14][C@@H:13]([C@@H:31]1[CH2:35][CH2:34][N:33]([C:36]2[C:37]([F:54])=[CH:38][N:39]3[C:44]([C:45]=2[CH3:46])=[C:43]([CH:47]2[CH2:49][CH2:48]2)[CH:42]=[C:41]([C:50]([OH:52])=[O:51])[C:40]3=[O:53])[CH2:32]1)[CH3:12]

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 9927245Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylateHCID 215713861-(t-Butoxycarbonylamino)ethyl-pyrrolidineHCID 867502981-cyclopropyl-8-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-7-fluoro-9-methyl-4-oxoquinolizine-3-carboxylic acid;hydrochloride

Produkt 1

HCID 512792(3R,1R)-8-(3-(1-Aminoethyl)pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A 0.35 g sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, and 0.73 g of sodium bicarbonate were dissolved in 24 mL of anhydrous acetonitrile, reacted with (3R, 1R)-3-(1-(t-butoxycarbonylamino)ethyl -pyrrolidine (0.51 g, prepared as described by Schroeder et al., J. Heterocyclic Chem., 29:1481-1498 (1992)), and carried forward as described in Example 253k-l to give the title product. mp 220°-222° C. MS 374 (M+H)+ ; 1H NMR (D6 -DMSO) ∂: 0.61 (m, 2H), 0.94 (m, 1H), 1.07 (m, 1H), 1.28 (d, 3H, J=6 Hz), 1.82 (m, 1H) 2.27 (m, 2H), 2.46 (m, 1H), 2.62 (s, 3H), 3.57 (s, 1H), 3.92 (m, 1H), 7.90 (s, 1H), 8.17 (br s, 3H), 9.07 (d, 1H, J=11 Hz), 13.84 (brs, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-9cf837b6bb464c4cb161028067f8f0dd
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599816

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