3-[2-(Pyrrolidin-1-yl)ethyl]aniline → (6-Bromo-4-(3-(2-(pyrrolidin-1-yl)ethyl)phenylamino)quinolin-3-yl)(cyclopropyl)methanone

HRID 2271673Notes

Reaction equation

HRID 2271673 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.[N:18]1([CH2:23][CH2:24][C:25]2[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=2)[NH2:28])[CH2:22][CH2:21][CH2:20][CH2:19]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]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:28][C:27]1[CH:29]=[CH:30][CH:31]=[C:25]([CH2:24][CH2:23][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[CH:26]=1

Participants

3

Reactant 2

HCID 219550223-[2-(Pyrrolidin-1-yl)ethyl]anilineHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66715504(6-Bromo-4-(3-(2-(pyrrolidin-1-yl)ethyl)phenylamino)quinolin-3-yl)(cyclopropyl)methanoneYield 74.6%

Procedure

Following general procedure C, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (197 mg, 0.635 mmol) was reacted with 3-[2-(pyrrolidin-1-yl)ethyl]aniline (120 mg, 0.635 mmol) to afford the desired product (220 mg, 74%) as a yellow solid: ESI MS m/z 464 [C25H26BrN3O+H]+.

Sources & evidence

ORD record
ord-1ffe27286509486e918ce4c3528f3daa
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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