2-(2,4-Dimethoxy-benzyl)-5-(4-methoxyquinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one → 5-(4-Methoxy-quinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 1591975Notes

Reaction equation

HRID 1591975 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:10](=[O:11])[CH2:9][N:8]([CH2:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17]([O:23][CH3:24])=[CH:18][CH:19]=[N:20]3)=[CH:15][CH:14]=2)[S:7]1(=[O:26])=[O:25]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:24][O:23][C:17]1[C:16]2[C:21](=[CH:22][C:13]([CH2:12][N:8]3[S:7](=[O:26])(=[O:25])[NH:6][C:10](=[O:11])[CH2:9]3)=[CH:14][CH:15]=2)[N:20]=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 671383182-(2,4-Dimethoxy-benzyl)-5-(4-methoxyquinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 101496175-(4-Methoxy-quinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

210 mg (459 μmol) of the title D compound, 2-(2,4-dimethoxy-benzyl)-5-(4-methoxy-quinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one are stirred for 30 min in 4 mL of 1:1 TFA/CH2Cl2. The solvent is removed on a rotary evaporator and the residue triturated with 4 mL of 1:1 MeCN/water. This mixture is filtered through a 0.2 micron disk and the solvent is removed. The resulting material is purified by preparative LC/MS, and the collected product fractions are lyophilized to give 5-(4-methoxy-quinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one: [M−1]−=306.

Workup

  1. customThe solvent is removed on a rotary evaporator
  2. customthe residue triturated with 4 mL of 1:1 MeCN/water
  3. filtrationThis mixture is filtered through a 0.2 micron disk
  4. customthe solvent is removed
  5. customThe resulting material is purified by preparative LC/MS

Sources & evidence

ORD record
ord-d41733d80a6941a1b16171ed62e632ee
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

Loading…