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

HRID 2271576Notes

Reaction equation

HRID 2271576 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]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2Cl.[CH2:18]([N:20]([CH2:28][CH3:29])[CH:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)[CH3:19]>>[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]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:27][CH:24]1[CH2:23][CH2:22][CH:21]([N:20]([CH2:28][CH3:29])[CH2:18][CH3:19])[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 349884N,N-Diethyl-1,4-cyclohexanediamineHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66716442{6-Bromo-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanoneYield 78%

Procedure

Following general procedure B, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (1.01 g, 3.25 mmol) was reacted with N1,N1-diethylcyclohexane-1,4-diamine (660 mg, 3.90 mmol) to afford the desired product (1.12 g, 78%) as a yellow wax: ESI MS m/z 523 [C23H30BrN3O+H]+.

Sources & evidence

ORD record
ord-7bb3bdeeb87e4fecb9e0944990d581b7
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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