2-Nitrobenzenesulfonyl chloride → N-(5-Morpholin-4-yl-quinolin-8-yl)-2-nitro-benzenesulfonamide

HRID 513814Notes

Reaction equation

HRID 513814 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27](Cl)(=[O:29])=[O:28])([O-:20])=[O:19]>N1C=CC=CC=1>[N:1]1([C:7]2[CH:16]=[CH:15][C:14]([NH:17][S:27]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N+:18]([O-:20])=[O:19])(=[O:28])=[O:29])=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[N:12]3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 145011628-Amino-5-morpholinoquinoline

Product 1

HCID 68182942N-(5-Morpholin-4-yl-quinolin-8-yl)-2-nitro-benzenesulfonamideYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 18 general procedure 26, 5-morpholin-4-yl-quinolin-8-ylamine 581 (154 mg, 0.67 mmol), 2-nitrobenzenesulfonyl chloride (148.86 mg, 0.67 mmol), and pyridine (1 ml) gave the title compound (216 mg, 78%) after purification by column chromatography with DCM/MeOH (100%-98:2 gradient) as the eluent.

Sources & evidence

ORD record
ord-3932990c64544007b26daa0358ac6e13
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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