Piperidine → HCID 59655017, compound

HRID 2053452Notes

Reaction equation

HRID 2053452 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11](OS(C(F)(F)F)(=O)=O)=[C:10]([C:27]2[O:31][N:30]=[C:29]([CH3:32])[CH:28]=2)[C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C1COCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11]([N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[C:10]([C:27]2[O:31][N:30]=[C:29]([CH3:32])[CH:28]=2)[C:9]1=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 59654957HCID 59654957, compound

Product 1

HCID 59655017HCID 59655017, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trifluoro-methanesulfonic acid 1-benzyl-6-chloro-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinolin-4-yl ester (25 mg, 0.050 mmol) in 1 ml of THF was added piperidine (17 mg, 0.20 mmol). The mixture was stirred at rt for 16 h. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (20% EtOAc/hexanes) gave 21.0 mg (97%) of product as a yellow green oil: 1H-NMR (CDCl3; 400 MHz) δ 7.93 (d, 1H, J=2.6 Hz), 7.37 (dd, 1H, J=9.0, 2.3 Hz), 7.18-7.33 (m, 6H), 6.56 (s, 1H), 5.50 (s, 2H), 2.99 (m, 4H), 2.40 (s, 3H), 1.64-1.76 (m, 6H). Mass spectrum (ESI, m/z): Calcd. for C25H24ClN3O2, 434.2 (M+H), found 434.1.

Workup

  1. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-07184b36f939469ca47c351d34e33bb7
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

Loading…