1-Hydroxybenzotriazole → N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,2-dimethylpropyl)-5-oxoprolinamide

HRID 2238527Notes

Reaction equation

HRID 2238527 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[CH2:3][N:4]1[C:11](=[O:12])[CH2:10][CH2:9][C@H:5]1[C:6]([OH:8])=O.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[Cl:37][C:38]1[C:43]([C:44]([F:47])([F:46])[F:45])=[CH:42][CH:41]=[CH:40][C:39]=1[CH2:48][NH2:49]>ClCCl>[Cl:37][C:38]1[C:43]([C:44]([F:46])([F:47])[F:45])=[CH:42][CH:41]=[CH:40][C:39]=1[CH2:48][NH:49][C:6](=[O:8])[C@@H:5]1[CH2:9][CH2:10][C:11](=[O:12])[N:4]1[CH2:3][C:2]([CH3:1])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 52242072-Chloro-3-(trifluoromethyl)benzylamineHCID 674591781-(2,2-Dimethylpropyl)-5-oxoproline

Product 1

HCID 67460075N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,2-dimethylpropyl)-5-oxoprolinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2,2-dimethylpropyl)-5-oxoproline (0.100 g, 0.5 mmol, prepared as described below) was dissolved in dichloromethane (5 ml) and to this was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.191 g, 1 mmol), and 1-hydroxybenzotriazole (0.135 g, 1 mmol). The mixture was stirred for 30 minutes at room temperature and then {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (0.209 g, 1 mmol) was added and the mixture was stirred overnight at room temperature. The mixture was then washed sequentially with water, 3N aqueous citric acid, and three more times with water then dried by filtering through a hydromatrix cartridge (Varian 5 g). The solvent was then evaporated and the residue was purified by mass-directed automated HPLC to give pure N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,2-dimethylpropyl)-5-oxoprolinamide.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. washThe mixture was then washed sequentially with water, 3N aqueous citric acid, and three more times with water
  3. customthen dried
  4. filtrationby filtering through a hydromatrix cartridge (Varian 5 g)
  5. customThe solvent was then evaporated
  6. customthe residue was purified

Sources & evidence

ORD record
ord-a8f31ff225624f3f9423b014309064ef
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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