Propionic Acid → N-({2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-(tri-fluoromethyl)pyrimidin-5-yl}methyl)propanamide

HRID 918769Notes

Reaction equation

HRID 918769 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:30])([F:29])[F:28])[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[C:18]([CH2:25][NH2:26])=[CH:17][N:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].C(N(CC)CC)C.[C:38](O)(=[O:41])[CH2:39][CH3:40]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:28])([F:29])[F:30])[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[C:18]([CH2:25][NH:26][C:38](=[O:41])[CH2:39][CH3:40])=[CH:17][N:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 594533771-{2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoromethyl)pyrimidin-5-yl}methanamine

Product 1

HCID 45378076N-({2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-(tri-fluoromethyl)pyrimidin-5-yl}methyl)propanamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-{2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoromethyl)pyrimidin-5-yl}methanamine (0.1 g) and triethylamine (0.05 g) were added to dichloromethane (20 mL), and then dichloromethane solution (10 mL) comprising anhydrous propionic acid (0.05 g) was added dropwise thereto under ice cooling. After the dropwise addition was completed, the reaction solution was stirred at room temperature for one hour. The solvent was evaporated off under reduced pressure, and the residue was then purified by a silica gel chromatography to obtain the title compound (0.1 g, 90%).

Workup

  1. additionAfter the dropwise addition
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue was then purified by a silica gel chromatography

Sources & evidence

ORD record
ord-b7a403057edf4756a922824cd0ce264b
Source dataset
uspto-grants-2016_03
Patent number
US09271499B2

Reaction notes

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