Dichloromethane → 5-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-N-{[4-(trifluoromethyl)phenyl]methyl}benzamide

HRID 1834999Notes

Reaction equation

HRID 1834999 reaction equation
ClCCl.[O:4]=[C:5]1[NH:9][C:8](=[O:10])[CH:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH:20]=2)[C:17]([OH:19])=O)[S:6]1.C(Cl)(=O)OCC.[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>C(N(CC)CC)C>[O:4]=[C:5]1[NH:9][C:8](=[O:10])[CH:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH:20]=2)[C:17]([NH:36][CH2:35][C:34]2[CH:33]=[CH:32][C:31]([C:30]([F:29])([F:39])[F:40])=[CH:38][CH:37]=2)=[O:19])[S:6]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10928Ethyl chloroformateHCID 768044-(Trifluoromethyl)benzylamineHCID 9943613HCID 9943613, compound

Product 1

HCID 1511835-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-N-{[4-(trifluoromethyl)phenyl]methyl}benzamideYield 61.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 49 mL of dichloromethane were added 6.30 g of triethylamine and 7.00 g of 5-[(2,4-dioxothiazolidin-5-yl) methyl]-2-methoxybenzoic acid. After 2.71 g of ethyl chlorocarbonate were added, the mixture was stirred for 10 minutes. Further, 4.59 g of 4-trifluoromethylbenzylamine were added and the mixture was stirred for 1 hour. After washed the reaction mixture with water, solvent was distilled off and to the residue were added 109 mL of water and 33 mL of ethanol, to which solution 2 mol/L hydrochloric acid was added dropwise to adjust to pH 2.0. The precipitated crystals were collected by filtration and washed with water to obtain 10.25 g of crude crystals. By recrystallizing 10.25 g of crude crystals twice from 90% ethanol, 6.49 g of 5-[(2,4-dioxothiazolidin-5-yl) methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl] benzamide (KRP-297) were obtained (yield 61.3%).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. washAfter washed the reaction mixture with water, solvent
  3. distillationwas distilled off and to the residue
  4. additionwere added 109 mL of water and 33 mL of ethanol
  5. additionto which solution 2 mol/L hydrochloric acid was added dropwise
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customto obtain 10.25 g of crude crystals
  9. customBy recrystallizing 10.25 g of crude crystals twice from 90% ethanol

Sources & evidence

ORD record
ord-5edc02e5500e46db913ed432caf4337b
Source dataset
uspto-grants-2004_08
Patent number
US06770133B2

Reaction notes

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