4-(Pyrrolidin-1-ylmethyl)aniline → {6-Bromo-4-[4-(pyrrolidin-1-ylmethyl)phenylamino]quinolin-3-yl}(cyclopropyl)methanone

HRID 2271656Notes

Reaction equation

HRID 2271656 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.[N:18]1([CH2:23][C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19]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:28][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 7768524-(Pyrrolidin-1-ylmethyl)anilineHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66715810{6-Bromo-4-[4-(pyrrolidin-1-ylmethyl)phenylamino]quinolin-3-yl}(cyclopropyl)methanoneYield 83.4%

Procedure

Following general procedure C, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (320 mg, 1.03 mmol) was reacted 4-(pyrrolidin-1-ylmethyl)aniline (385 mg, 1.55 mmol) to afford the desired product (387 mg, 83%) as a yellow solid: ESI MS m/z 450 [C24H24BrN3O+H]+.

Sources & evidence

ORD record
ord-ceb2df8b45624848ba669f4b46c0e317
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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