5-Chloroquinolin-8-amine → Pyridine-3-sulfonic acid (5-chloro-quinolin-8-yl)-amide

HRID 513432Notes

Reaction equation

HRID 513432 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:14]=1>>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:19]([C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)(=[O:21])=[O:20])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

3

Reactant 2

HCID 2248605-Chloroquinolin-8-amine2×HCID 3164136Pyridine-3-sulfonyl chloride2×

Product 1

HCID 60163925Pyridine-3-sulfonic acid (5-chloro-quinolin-8-yl)-amideYield 43%

Procedure

In a similar fashion using route 14 general procedure 26, 5-chloroquinolin-8-amine (Intermediate 27) (50 mg, 0.28 mmol), pyridine-3-sulfonyl chloride (Intermediate 17) (74 mg, 0.42 mmol) gave the title compound (38 mg, 43%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-c4a79b7e147d4d16b8f43312146177be
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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