5-Chloroquinolin-8-amine → HCID 68183167, compound

HRID 513533Notes

Reaction equation

HRID 513533 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.[CH3:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1)(=[O:16])=[O:15]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:23]([C:20]2[CH:21]=[CH:22][C:17]([S:14]([CH3:13])(=[O:16])=[O:15])=[CH:18][C:19]=2[N+:27]([O-:29])=[O:28])(=[O:24])=[O:25])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 2

HCID 2248605-Chloroquinolin-8-amine2×HCID 61728228HCID 61728228, compound2×

Product 1

HCID 68183167HCID 68183167, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

In the similar fashion using route 14 general procedure 27, 5-chloro-quinolin-8-ylamine (Intermediate 27) (200 mg, 1.12 mmol), 4-methanesulfonyl-2-nitro-benzenesulfonyl chloride (Intermediate 439) (456 mg, 1.46 mmol), DMAP (cat.) and pyridine (5 ml) gave the title compound (350 mg, 60%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-53315d8e69444474ab872ff52327fc5f
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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