1-(6-Bromo-4-chloroquinolin-3-YL)ethanone → Tert-butyl (1-(5-((3-acetyl-6-bromoquinolin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)(methyl)carbamate

HRID 2271543Notes

Reaction equation

HRID 2271543 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:14])[CH3:13])=[C:5]2Cl.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH:25]([N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24]2)=[N:21][CH:22]=1>>[C:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][CH2:26][CH:25]([N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:24]3)=[N:21][CH:22]=1)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 667154831-(6-Bromo-4-chloroquinolin-3-YL)ethanoneHCID 86692851Tert-butyl (1-(5-aminopyridin-2-yl)piperidin-3-yl)(methyl)carbamate

Product 1

HCID 86692852Tert-butyl (1-(5-((3-acetyl-6-bromoquinolin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)(methyl)carbamateYield 80.4%

Procedure

Following general procedure C, 1-(6-bromo-4-chloroquinolin-3-yl)ethanone (285 mg, 1.0 mmol) was reacted with tert-butyl (1-(5-aminopyridin-2-yl)piperidin-3-yl)(methyl)carbamate (442 mg, 1.45 mmol) to afford the desired product (446 mg, 80%) as an orange-red solid. ESI MS m/z 554 [C27H32BrN5O3+H]+

Sources & evidence

ORD record
ord-af779a84e212482ba308dd42ff24db89
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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