Benzenesulfonyl chloride → HCID 60164004, compound

HRID 513479Notes

Reaction equation

HRID 513479 reaction equation
[Cl:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([NH2:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([NH:13][S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 68183356HCID 68183356, compound2×

Product 1

HCID 60164004HCID 60164004, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 5-chloro-6-methylquinolin-8-amine (Intermediate 51) (160 mg, 0.83 mmol), benzenesulfonyl chloride (175 mg, 0.99 mmol) and DMAP (cat.) gave the title compound (110 mg, 40%) after purification by column chromatography with n-hexane/EtOAc (1:1), followed by DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-088e93e233ba4fb180df05167d7833f3
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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