1-(6-Bromo-4-chloroquinolin-3-yl)-3-methylbutan-1-one → HCID 178446972, compound

HRID 2271596Notes

Reaction equation

HRID 2271596 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:17])[CH2:13][CH:14]([CH3:16])[CH3:15])=[C:5]2Cl.[NH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]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](=[O:17])[CH2:13][CH:14]([CH3:16])[CH3:15])=[C:5]2[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 866928431-(6-Bromo-4-chloroquinolin-3-yl)-3-methylbutan-1-oneHCID 178419079HCID 178419079, compound

Product 1

HCID 178446972HCID 178446972, compoundYield 56%

Procedure

Following general procedure B, 1-(6-bromo-4-chloroquinolin-3-yl)-3-methylbutan-1-one (309 mg, 0.950 mmol) was reacted with tert-butyl trans-4-aminocyclohexylcarbamate (407 mg, 1.90 mmol) to afford the desired product (267 mg, 56%) as a yellow solid: ESI MS m/z 504 [C20H26BrN3O+H]+.

Sources & evidence

ORD record
ord-4b4483c61e9b488ebdbfdc8faea4ab1d
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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