HCID 18372591, compound → HCID 18372554, compound

HRID 1069516Notes

Reaction equation

HRID 1069516 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([S:12]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)(=[O:14])=[O:13])[C:9]([O:24]C)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([S:12]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)(=[O:13])=[O:14])[C:9]([OH:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

3

Reactant 1

HCID 18372591HCID 18372591, compound

Product 1

HCID 18372554HCID 18372554, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2, a flame-dried, 50-mL, two-necked flask is charged with 5-chloro-N-[(4-chlorophenyl)methyl]-8-methoxy-7-quinolinesulfonamide (0.322 g), which is the first title compound of Preparation 9, and CH2Cl2 (20 mL) and is cooled in a dry ice/acetone bath. 1.0 M BBr3 (1.05 mL) is added dropwise. The cooling bath is removed and the reaction mixture is allowed to stir for 1.5 hrs. It is then poured into 75 mL 5% NaHCO3 aqueous solution, and the layers are separated. The aqueous layer is extracted twice with CH2Cl2. The combined organic layers are washed with H2O and then brine, dried over MgSO4, filtered and concentrated to a brown residue. Purification by column chromatography (elution with 2-5% MeOH/ CH2Cl2 with <1% AcOH) yields 0.037 g of the title compound as a pale yellow solid.

Sources & evidence

ORD record
ord-388c83f25a334e8d89dcb3a0de000537
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

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