HCID 59822488, compound → HCID 59822470, compound

HRID 2425766Notes

Reaction equation

HRID 2425766 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[C:9]([CH3:14])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:15]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)=[O:16])[C:5]1=[O:32])([CH3:3])[CH3:2]>Cl.CO>[CH:1]([N:4]1[C:13]2[C:8](=[C:9]([CH3:14])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:15]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:16])[C:5]1=[O:32])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59822488HCID 59822488, compound

Product 1

HCID 59822470HCID 59822470, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-({[(1-isopropyl-5-methyl-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]amino}methyl)piperidine-1-carboxylate (15.0 g, 32.6 mmol, step 3) in 10% hydrogen chloride in methanol was stirred at room temperature for 12 h. Then, the solvent was removed in vacuo to give the title compound as hydrochloride salt. This salt was poured onto saturated aqueous sodium hydrogen carbonate solution (500 mL), and the aqueous layer was extracted with dichloromethane (500 mL×5). The combined organic layer was dried over magnesium sulfate and sodium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of aminopropyl silica gel eluting with methanol/dichloromethane (1:10) to give 10.3 g (92%) of the title compound as a pale yellow amorphous.

Workup

  1. customThen, the solvent was removed in vacuo

Sources & evidence

ORD record
ord-96eaadc5de2f412bafe0acafd1ff4693
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

Loading…