1-(6-Bromo-4-chloroquinolin-3-YL)ethanone → 1-(6-bromo-4-((1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-yl)amino)quinolin-3-yl)ethanone

HRID 2271544Notes

Reaction equation

HRID 2271544 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.[CH3:16][N:17]1[CH2:21][CH2:20][CH:19]([N:22]2[CH:26]=[C:25]([NH2:27])[CH:24]=[N:23]2)[CH2:18]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:27][C:25]1[CH:24]=[N:23][N:22]([CH:19]2[CH2:20][CH2:21][N:17]([CH3:16])[CH2:18]2)[CH:26]=1

Participants

3

Reactant 2

HCID 667154831-(6-Bromo-4-chloroquinolin-3-YL)ethanoneHCID 679816411-(1-Methyl-3-pyrrolidinyl)-1H-pyrazol-4-amine

Product 1

HCID 667163161-(6-bromo-4-((1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-yl)amino)quinolin-3-yl)ethanoneYield 87%

Procedure

Following general procedure C, 1-(6-bromo-4-chloroquinolin-3-yl)ethanone (285 mg, 1.0 mmol) was reacted with 1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-amine (0.28 g, 1.68 mmol) to afford the desired product (360 mg, 87%) as a light yellow solid. ESI MS m/z 414 [C19H20BrN5O+H]+

Sources & evidence

ORD record
ord-dac55086e63b49a785c25ad9e05ad27c
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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