2-[(5-Aminopyridin-2-yl)amino]ethanol → (6-Bromo-4-(6-(2-hydroxyethylamino)pyridin-3-ylamino)quinolin-3-yl)(cyclopropyl)methanone

HRID 2271635Notes

Reaction equation

HRID 2271635 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.[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([NH:25][CH2:26][CH2:27][OH:28])=[N:23][CH:24]=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:18][C:19]1[CH:24]=[N:23][C:22]([NH:25][CH2:26][CH2:27][OH:28])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 30153332-[(5-Aminopyridin-2-yl)amino]ethanolHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66715337(6-Bromo-4-(6-(2-hydroxyethylamino)pyridin-3-ylamino)quinolin-3-yl)(cyclopropyl)methanoneYield 67.2%

Procedure

Following General procedure C, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (311 mg, 1 mmol) was reacted with 2-(5-aminopyridin-2-ylamino)ethanol (230 mg, 1.5 mmol) to afford the desired product (287 mg, 67%) as a yellow solid: ESI MS m/z 427 [C20H19BrN4O2+H]+.

Sources & evidence

ORD record
ord-72b68475ebe348bd817328c242b20796
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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