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

HRID 1776992
Notes
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Reaction equation

HRID 1776992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:26]([F:29])([F:28])[F:27])[CH2:14][CH2:13][N:12]([C:15]3[S:16][C:17]([CH2:24][NH2:25])=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].C(N(CC)CC)C.[C:37](O)(=[O:40])[CH2:38][CH3:39]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:26]([F:29])([F:27])[F:28])[CH2:14][CH2:13][N:12]([C:15]3[S:16][C:17]([CH2:24][NH:25][C:37](=[O:40])[CH2:38][CH3:39])=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 594533691-{2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazol-5-yl}methanamine

Product 1

HCID 45378077N-({2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazol-5-yl}methyl)propanamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

1-{2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoro-methyl)-1,3-thiazol-5-yl}methanamine (0.1 g) and triethylamine (0.05 g) were added to dichloromethane (20 mL), followed by the dropwise addition of dichloromethane solution (10 mL) comprising anhydrous propionic acid (0.05 g) 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-d512c034fde84ceeadc89651094d1ece
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266830B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes