N2-(2-(dimethylamino)ethyl)pyridine-2,5-diamine → (6-Bromo-4-(6-(2-(dimethylamino)ethylamino)pyridine-3-ylamino)quinolin-3-yl)(cyclopropyl)methanone

HRID 2271636Notes

Reaction equation

HRID 2271636 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.[CH3:18][N:19]([CH3:30])[CH2:20][CH2:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][N: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:29][C:26]1[CH:25]=[N:24][C:23]([NH:22][CH2:21][CH2:20][N:19]([CH3:30])[CH3:18])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 16772731N2-(2-(dimethylamino)ethyl)pyridine-2,5-diamineHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66715789(6-Bromo-4-(6-(2-(dimethylamino)ethylamino)pyridine-3-ylamino)quinolin-3-yl)(cyclopropyl)methanoneYield 66%

Procedure

Following General procedure C, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (311 mg, 1 mmol) was reacted with N2-(2-(dimethylamino)ethyl)pyridine-2,5-diamine (270 mg, 1.5 mmol) to afford the desired product (300 mg, 66%) as a yellow solid: ESI MS m/z 454 [C22H24BrN5O+H]+.

Sources & evidence

ORD record
ord-8fba51da399d46b2a0fcfddd8af464cf
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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