Tetrahydrofuran → N-{1-[7-(1-Aminoethyl)-5-chloroquinolin-8-yl]piperidin-4-yl}methanesulfonamide

HRID 1192649Notes

Reaction equation

[C:1]([C:4]1[C:13]([N:14]2[CH2:19][CH2:18][CH:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:16][CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:25])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:32].[Na+].O1CCCC1>CO.C(#N)C>[NH2:32][CH:1]([C:4]1[C:13]([N:14]2[CH2:19][CH2:18][CH:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:16][CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:25])[CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of N-[1-(7-acetyl-5-chloroquinolin-8-yl)piperidin-4-yl]methanesulfonamide (0.027 g, 0.071 mmol) and ammonium acetate (0.0545 g, 0.707 mmol) in methanol (0.3 mL) and acetonitrile (0.3 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.17 mL, 0.17 mmol). The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution, extracted with dichloromethane, dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C17H24ClN4O2S (M+H)+: m/z=383.1; Found: 383.1.

Workup

temperatureAfter cooling to room temperature, to the resulting mixture
temperatureThe reaction was heated at 65° C. overnight
temperatureThe mixture was cooled to room temperature
customquenched with sat. NaHCO3 solution
extractionextracted with dichloromethane
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-abdc9679d3cd45f6b928f4db0c34d0cf
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

Loading…