Trifluoroacetic acid → HCID 178477885, compound

HRID 1055030Notes

Reaction equation

HRID 1055030 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([CH2:12][CH2:13][C:14]3[N:18]=[C:17]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[N:16](CC4C=CC(OC)=CC=4)[N:15]=3)=[N:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[OH-].[Na+]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([CH2:12][CH2:13][C:14]3[N:18]=[C:17]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[NH:16][N:15]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 14798Sodium HydroxideHCID 900172007-chloro-2-(2-(1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethyl)quinoxaline

Product 1

HCID 178477885HCID 178477885, compoundYield 17.7%

Procedure

7-chloro-2-(2-(1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethyl)quinoxaline (17 mg, 37.9 μmol, Eq: 1.00) was stirred in trifluoroacetic acid (173 mg, 117 μl, 1.51 mmol, Eq: 40) with anisole (81.9 mg, 82.7 μl, 757 μmol, Eq: 20) at 120° C. overnight. The mixture was made basic by addition of sodium hydroxide 2N aq. and extracted three times with 1,2-dichloromethane, dried over magnesium sulfate, filtered and evaporated. The crude material was applied on silica gel and purified by column chromatography to give 7-Chloro-2-[2-(5-pyrrolidin-1-yl-1H-[1,2,4]triazol-3-yl)-ethyl]-quinoxaline (2.2 mg, 17.7%) as off-white solid. MS: m/z=329.12 (M+H+)

Workup

  1. extractionextracted three times with 1,2-dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-87749cb36df243a89dff82c87684dc67
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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