1-(5-Aminopyridin-2-yl)pyrrolidin-3-ol → (6-Bromo-4-(6-(3-hydroxypyrrolidin-1-yl)pyridin-3-ylamino)quinolin-3-yl)(cyclopropyl)methanone

HRID 2271633Notes

Reaction equation

HRID 2271633 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]([N:25]2[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26]2)=[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]([N:25]2[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26]2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 534081671-(5-Aminopyridin-2-yl)pyrrolidin-3-olHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 86692885(6-Bromo-4-(6-(3-hydroxypyrrolidin-1-yl)pyridin-3-ylamino)quinolin-3-yl)(cyclopropyl)methanoneYield 51.6%

Procedure

Following General procedure C, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (311 mg, 1 mmol) was reacted with 1-(5-aminopyridin-2-yl)pyrrolidin-3-ol (269 mg, 1.5 mmol) to afford the desired product (234 mg, 51%) as a yellow solid: ESI MS m/z 453 [C22H21BrN4O2+H]+.

Sources & evidence

ORD record
ord-a291c53a360846ebbbfd4aaa7be822b3
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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