(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone → {6-Bromo-4-[5-(2-(pyrrolidin-1-yl)ethyl)pyridin-3-ylamino]quinolin-3-yl}(cyclopropyl)methanone

HRID 2271676Notes

Reaction equation

HRID 2271676 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]([NH2:31])[CH:28]=[N:29][CH:30]=2)[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:31][C:27]1[CH:28]=[N:29][CH:30]=[C:25]([CH2:24][CH2:23][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:26]=1

Participants

3

Reactant 2

HCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanoneHCID 667157365-(2-(Pyrrolidin-1-yl)ethyl)pyridin-3-amine

Product 1

HCID 86692896{6-Bromo-4-[5-(2-(pyrrolidin-1-yl)ethyl)pyridin-3-ylamino]quinolin-3-yl}(cyclopropyl)methanoneYield 45.3%

Procedure

Following general procedure C, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (262 mg, 0.845 mmol) was reacted with 5-[2-(pyrrolidin-1-yl)ethyl]pyridin-3-amine (161 mg, 0.845 mmol) to afford the desired product (178 mg, 45%) as a white solid: ESI MS m/z 465 [C24H25BrN4O+H]+.

Sources & evidence

ORD record
ord-a22dcf56d76e44fdafd4987cf02fe534
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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