N,N-Diethyl-1,4-cyclohexanediamine → 1-{6-Bromo-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}ethanone

HRID 2271595Notes

Reaction equation

HRID 2271595 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.[CH2:16]([N:18]([CH2:26][CH3:27])[CH:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1)[CH3:17]>>[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:25][CH:22]1[CH2:21][CH2:20][CH:19]([N:18]([CH2:26][CH3:27])[CH2:16][CH3:17])[CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 349884N,N-Diethyl-1,4-cyclohexanediamineHCID 667154831-(6-Bromo-4-chloroquinolin-3-YL)ethanone

Product 1

HCID 667157931-{6-Bromo-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}ethanoneYield 92%

Procedure

Following general procedure B, 1-(6-bromo-4-chloroquinolin-3-yl)ethanone (116 mg, 0.408 mmol) was reacted with N1,N1-diethylcyclohexane-1,4-diamine (138 mg, 0.812 mmol) to afford the desired product (157 mg, 51%) as an off-white solid: ESI MS m/z 418 [C21H28BrN3O+H]+.

Sources & evidence

ORD record
ord-33a45757fccb420c986007ffdc54ff93
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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