Cyclopropanecarbonyl chloride → N-{[6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)-pyrrolidin-1-yl}-4-(trifluoromethyl)pyridin-3-yl]methyl}cyclopropanecarboxamide

HRID 2206919Notes

Reaction equation

HRID 2206919 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]2([C:30]([F:33])([F:32])[F:31])[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([CH2:24][NH2:25])=[C:20]([C:26]([F:29])([F:28])[F:27])[CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:36]1([C:39](Cl)=[O:40])[CH2:38][CH2:37]1>C(Cl)Cl>[F:35][C:2]([F:1])([F:34])[C:3]1[CH:4]=[C:5]([C:13]2([C:30]([F:31])([F:32])[F:33])[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([CH2:24][NH:25][C:39]([CH:36]4[CH2:38][CH2:37]4)=[O:40])=[C:20]([C:26]([F:27])([F:28])[F:29])[CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 871606231-[6-{3-[3,5-Bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)-pyrrolidin-1-yl}-4-(trifluoromethyl)pyridin-3-yl]methanamine

Product 1

HCID 87160648N-{[6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)-pyrrolidin-1-yl}-4-(trifluoromethyl)pyridin-3-yl]methyl}cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[6-{3-[3,5-Bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-4-(trifluoromethyl)pyridin-3-yl]methanamine (0.18 g) was dissolved in methylene chloride (5 ml), and to the solution was added cyclopropane carbonyl chloride (0.036 ml) at room temperature. The reaction mixture was stirred overnight and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the target compound (0.15 g).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1fedac5986b143ce994fceb135fcf607
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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