Triethylamine → 8-[3-(N-Boc-Aminoethyl)Pyrrolidinyl]-1-Ethyl-9-Methoxy-4-Oxo-4H-Quinolizine-3-Carboxylic Acid Ethyl Ester

HRID 1635094Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([O:18][CH3:19])=[C:11](Cl)[CH:12]=[CH:13]2)=[C:8]([CH2:20][CH3:21])[CH:7]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:29]([NH:36][CH2:37][CH2:38][CH:39]1[CH2:43][CH2:42][NH:41][CH2:40]1)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([O:18][CH3:19])=[C:11]([N:41]3[CH2:42][CH2:43][CH:39]([CH2:38][CH2:37][NH:36][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:40]3)[CH:12]=[CH:13]2)=[C:8]([CH2:20][CH3:21])[CH:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

Ethyl-8-chloro-1-ethyl-9-methoxy-4-oxo-4H-quinolizine-3-carboxylate (Precursor A) (0.151 g) and triethylamine (0.5 ml) are dissolved in acetonitrile (6 ml). To this solution 3-(N-boc-aminoethyl)pyrrolidine (Precursor D) (0.215 g) is added and the solution stirred at 40° C. for 18 hours. The solvent is evaporated and the residue dissolved in dichloromethane, washed with 1N hydrochloric acid and dried over sodium sulfate. The desired product is obtained by evaporation of the solvent.

Workup

customThe solvent is evaporated
dissolutionthe residue dissolved in dichloromethane
washwashed with 1N hydrochloric acid
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-c85d9ddc9cb04eba93f66c39a505a5a1
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509349B1

Reaction notes

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