Benzenesulfonyl chloride → Methyl 6-[(phenylsulfonyl)amino]-5-quinolinecarboxylate

HRID 1725879Notes

Reaction equation

HRID 1725879 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[C:16]1([S:22]([NH:1][C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=2[C:12]([O:14][CH3:15])=[O:13])(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 45089602Methyl 6-aminoquinoline-5-carboxylate

Product 1

HCID 68863977Methyl 6-[(phenylsulfonyl)amino]-5-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Example 96B (0.233 g, 1.20 mmol) in pyridine (4 mL) was treated with benzenesulfonyl chloride (0.20 mL, 1.6 mmol), and stirred for 7 hours at ambient temperature. The mixture was concentrated and the residue was purified by C18 reverse-phase HPLC with acetonitrile/water/0.5 mM ammonium acetate to provide the desired product. MS (ESI(+)) m/e 343 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by C18 reverse-phase HPLC with acetonitrile/water/0.5 mM ammonium acetate

Sources & evidence

ORD record
ord-d00d49023bb94e668c2bd4d670f63c34
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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