Heptanoyl chloride → N-[4-({2-[2-(methylsulfonyl)ethoxy]ethyl}amino)quinoline-3-yl]heptanamide hydrochloride

HRID 547312Notes

Reaction equation

HRID 547312 reaction equation
[C:1]([Cl:9])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:10][S:11]([CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[NH2:30])(=[O:13])=[O:12]>C(#N)C>[ClH:9].[CH3:10][S:11]([CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[NH:30][C:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 17313Heptanoyl chlorideHCID 86064731N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine

Product 1

HCID 67203329N-[4-({2-[2-(methylsulfonyl)ethoxy]ethyl}amino)quinoline-3-yl]heptanamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Heptanoyl chloride (1 mL, 6.5 mmol) was added dropwise to a solution of N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine (prepared as described in Parts A-E of Example 1, approximately 1.8 g, approximately 5.9 mmol) in acetonitrile (30 mL). The reaction mixture was allowed to stir for 1 hour at room temperature, then was concentrated under reduced pressure to yield N-[4-({2-[2-(methylsulfonyl)ethoxy]ethyl}amino)quinoline-3-yl]heptanamide hydrochloride as an orange foam that was used without purification.

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-59cff49f07424182a3fa6e10d8f1f198
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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