Diethylamine → N-(4-Diethylamino-quinolin-8-yl)-benzenesulfonamide

HRID 513754Notes

Reaction equation

HRID 513754 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23].CCN(C(C)C)C(C)C>C(O)CCC>[CH2:22]([N:24]([CH2:25][CH3:26])[C:2]1[C:11]2[C:6](=[C:7]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)[CH3:23]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 68183402N-(4-Chloro-quinolin-8-yl)-benzenesulfonamide

Product 1

HCID 68183484N-(4-Diethylamino-quinolin-8-yl)-benzenesulfonamideYield 27%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In a similar fashion using route 48 general procedure 114, N-(4-chloro-quinolin-8-yl)-benzenesulfonamide 224 (100 mg, 0.32 mmol), diethyl amine (0.097 ml, 0.94 mmol), DIPEA (0.11 ml, 0.63 mmol) and n-butanol (1 ml) gave the title compound (30 mg, 27%) after purification by column chromatography with chloroform/MeOH (1 drop NH3) (97:3) as the eluent.

Sources & evidence

ORD record
ord-881f307873864ddb811f3156ce05cce5
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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