1-(6-Bromo-4-chloroquinolin-3-YL)ethanone → 1-(6-bromo-4-((1-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)amino)quinolin-3-yl)ethanone

HRID 2271548Notes

Reaction equation

HRID 2271548 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2Cl.Cl.Cl.[CH3:18][N:19]([CH3:30])[CH:20]1[C:28]2[C:23](=[CH:24][C:25]([NH2:29])=[CH:26][CH:27]=2)[CH2:22][CH2:21]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:29][C:25]1[CH:24]=[C:23]2[C:28](=[CH:27][CH:26]=1)[CH:20]([N:19]([CH3:30])[CH3:18])[CH2:21][CH2:22]2

Participants

3

Reactant 2

HCID 667154831-(6-Bromo-4-chloroquinolin-3-YL)ethanoneHCID 86692854N1,N1-dimethyl-2,3-dihydro-1H-indene-1,5-diamine dihydrochloride

Product 1

HCID 667162041-(6-bromo-4-((1-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)amino)quinolin-3-yl)ethanoneYield 5.5%

Procedure

Following general procedure C, 1-(6-bromo-4-chloroquinolin-3-yl)ethanone (256 mg, 0.90 mmol) was reacted with N1,N1-dimethyl-2,3-dihydro-1H-indene-1,5-diamine dihydrochloride (0.814 mmol) to afford the desired product (19 mg, 5.5%) as a yellow-brown solid. ESI MS m/z 424 [C22H22BrN3O+H]+

Sources & evidence

ORD record
ord-32ca9e27994842a5baa005e3a194d4b5
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…