8-Aminoquinoline → 6-Cyano-pyridine-3-sulfinic acid quinolin-8-ylamide

HRID 513463Notes

Reaction equation

HRID 513463 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:12]([C:14]1[N:19]=[CH:18][C:17]([S:20](Cl)(=O)=[O:21])=[CH:16][CH:15]=1)#[N:13]>CN(C1C=CN=CC=1)C>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][S:20]([C:17]2[CH:18]=[N:19][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)=[O:21])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 470031906-Cyanopyridine-3-sulfonyl chloride

Product 1

HCID 681831166-Cyano-pyridine-3-sulfinic acid quinolin-8-ylamideYield 26.9%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 18 general procedure 27, 8-aminoquinoline (200 mg, 1.39 mmol), 6-cyanopyridine-3-sulfonyl chloride 19 (337 mg, 1.66 mmol) and DMAP (cat.) gave the title compound (110 mg, 25%) after purification by column chromatography with n-hexane/EtOAc (4:1) as the eluent.

Sources & evidence

ORD record
ord-37eec6288a844527a0c3f7253ecf11ed
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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