1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-amine → 1-(6-bromo-4-((1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)quinolin-3-yl)ethanone

HRID 2271542Notes

Reaction equation

HRID 2271542 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[CH2:22][CH2:21][CH:20]([N:23]2[CH:27]=[C:26]([NH2:28])[CH:25]=[N:24]2)[CH2:19][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:28][C:26]1[CH:25]=[N:24][N:23]([CH:20]2[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]2)[CH:27]=1

Participants

3

Reactant 2

HCID 533023461-(1-methylpiperidin-4-yl)-1H-pyrazol-4-amineHCID 667154831-(6-Bromo-4-chloroquinolin-3-YL)ethanone

Product 1

HCID 667160841-(6-bromo-4-((1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)quinolin-3-yl)ethanoneYield 52.1%

Procedure

Following general procedure C, 1-(6-bromo-4-chloroquinolin-3-yl)ethanone (285 mg, 1.0 mmol) was reacted with 1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-amine (0.30 g, 1.66 mmol) to afford the desired product (223 mg, 52%) as a light yellow solid. ESI MS m/z 428 [C20H22BrN5O+H]+

Sources & evidence

ORD record
ord-f797d76638a8462c8b44b96ab6989276
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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