N,N-Diethyl-1,4-cyclohexanediamine → N1-[6-Bromo-3-(methylsulfonyl)quinolin-4-yl]-N4,N4-diethylcyclohexane-1,4-diamine

HRID 2271590Notes

Reaction equation

HRID 2271590 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]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2Cl.[CH2:17]([N:19]([CH2:27][CH3:28])[CH:20]1[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1)[CH3:18]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[NH:26][CH:23]1[CH2:22][CH2:21][CH:20]([N:19]([CH2:27][CH3:28])[CH2:17][CH3:18])[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 349884N,N-Diethyl-1,4-cyclohexanediamineHCID 667152456-Bromo-4-chloro-3-(methylsulfonyl)quinoline

Product 1

HCID 68092001N1-[6-Bromo-3-(methylsulfonyl)quinolin-4-yl]-N4,N4-diethylcyclohexane-1,4-diamineYield 87%

Procedure

Following general procedure B, 6-bromo-4-chloro-3-(methylsulfonyl)quinoline (161 mg, 0.500 mmol) was reacted with N1,N1-diethylcyclohexane-1,4-diamine (170 mg, 1.00 mmol) to afford the desired product (197 mg, 87%) as a white solid: ESI MS m/z 454 [C20H28BrN3O2S+H]+.

Sources & evidence

ORD record
ord-a72b8abb1f074b2bafe6193c9fd60684
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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