Reaktion #1972

ord-42ec8884ab714360a71d7169f934632f

Reaktionsgleichung

CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O
8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester
C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1
(3R,1S)-3-(1-(t-butoxycarbonylamino)ethyl)pyrrolidine
Cc1c(N2CC[C@@H]([C@H](C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl
title product
Cc1c(N2CC[C@@H]([C@H](C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl
(3R,1 S)-8-(3-(1-Aminoethyl)pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

A sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in anhydrous acetonitrile, reacted with (3R,1S)-3-(1-(t-butoxycarbonylamino)ethyl)pyrrolidine (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 250°-255° C. (dec.). MS 374 (M+H)+ ; 1H NMR (D6 -DMSO) ∂: 0.59 (m, 2H), 1.00 (m, 2H), 1.29 (d, 3H, J=6 Hz), 1.77 (m, 1H), 2.13 (m, 1H), 2.29 (m, 1H), 2.41 (m, 1H), 2.64 (s, 3H), 3.57 (s, 1H), 3.76 (m, 3H), 3.94 (m, 1H), 7.91 (s, 1H), 8.17 (brs, 3H), 9.07 (d, 1H, J=11 Hz), 13.83 (brs, 1H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726182uspto-grants-1998_03