N,N-Dimethylethylenediamine → N-[4-(2-Dimethylamino-ethylamino)-quinolin-8-yl]-benzenesulfonamide

HRID 513753Notes

Reaction equation

[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].CCN(C(C)C)C(C)C.Cl[C:17]1[C:26]2[C:21](=[C:22]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:30])=[O:29])[CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][CH:18]=1>C(O)CCC>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:17]1[C:26]2[C:21](=[C:22]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:29])=[O:30])[CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N,N-dimethylethylenediamine (0.10 ml, 0.95 mmol) and DIPEA (0.11 ml, 0.63 mmol) were added to a solution of N-(4-chloro-quinolin-8-yl)-benzenesulfonamide 224 (100 mg, 0.32 mmol) in n-butanol (1 ml) and the reaction was heated in a sealed tube at 100° C. for 16 h. After cooling, the mixture was concentrated in vacuo. The crude residue was purified by column chromatography with chloroform/MeOH (97:3) as the eluent to give the title compound (40 mg, 34%).

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated in vacuo
customThe crude residue was purified by column chromatography with chloroform/MeOH (97:3) as the eluent

Sources & evidence

ORD record: ord-f892b101069d4a2da70b47fd248d9cdb
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

Loading…