Benzenemethanamine, 4-amino-N,N-dimethyl- → 1-(6-Bromo-4-(4-((dimethylamino)methyl)phenylamino)quinolin-3-yl)-2-methylpropan-1-one

HRID 2271603Notes

Reaction equation

HRID 2271603 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:16])[CH:13]([CH3:15])[CH3:14])=[C:5]2Cl.[CH3:18][N:19]([CH2:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)[CH3:20]>>[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:16])[CH:13]([CH3:15])[CH3:14])=[C:5]2[NH:26][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:19]([CH3:20])[CH3:18])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 308051Benzenemethanamine, 4-amino-N,N-dimethyl-HCID 680919931-(6-Bromo-4-chloroquinolin-3-yl)-2-methylpropan-1-one

Product 1

HCID 866928741-(6-Bromo-4-(4-((dimethylamino)methyl)phenylamino)quinolin-3-yl)-2-methylpropan-1-oneYield 27.2%

Procedure

Following general procedure B, 1-(6-bromo-4-chloroquinolin-3-yl)-2-methylpropan-1-one (604 mg, 1.93 mmol) was reacted with 4-((dimethylamino)methyl)aniline (882 mg, 3.87 mmol) to afford the desired product (224 mg, 27%) as a yellow solid: ESI MS m/z 432, [C22H30BrN3O+H]+

Sources & evidence

ORD record
ord-45c94ae14afe413db65795109567d80e
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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