4-Methoxybenzenesulfonyl chloride → HCID 178492881, compound

HRID 2290030Notes

Reaction equation

HRID 2290030 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]=[CH:7][C:6]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:14])=[C:5]2[OH:24].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>N1C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:13]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[OH:24])=[CH:3][C:2]([NH:1][S:33]([C:30]2[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=2)(=[O:35])=[O:34])=[CH:11][C:10]=3[F:12])=[O:14])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 178507808HCID 178507808, compound

Product 1

HCID 178492881HCID 178492881, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a flask containing 6-amino-N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-3-quinolinecarboxamide from Example No. 186 (0.06 g) and pyridine (1.5 mL) is added 4-methoxyphenylsulfonyl chloride (0.04 g). The reaction mixture is stirred for 2 hours then concentrated under reduced pressure. The residue is triturated with toluene (2×) and dried in vacuo. The residue is adsorbed onto silica and chromatographed on silica eluting with 2% MeOH:CH2Cl2 to 6% MeOH:CH2Cl2. The product-containing fractions are evaporated to give 0.04 g of the title compound as a white solid.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue is triturated with toluene (2×)
  3. customdried in vacuo
  4. customchromatographed on silica eluting with 2% MeOH
  5. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-f7729d01f2ca402d903890a76e7e1dc4
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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