Isopropylamine → HCID 59214290, compound

HRID 2244642Notes

Reaction equation

HRID 2244642 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:21]=[CH:20][CH:19]=[C:18]4[C:14]=3[CH:15]=[CH:16][NH:17]4)[N:9]=2)=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].[CH3:26][CH:27]([NH2:29])[CH3:28]>C1COCC1>[NH:17]1[C:18]2[C:14](=[C:13]([C:10]3[N:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:29][CH:27]([CH3:28])[CH3:26])=[C:3]([C:22]([F:25])([F:23])[F:24])[CH:4]=4)[O:12][N:11]=3)[CH:21]=[CH:20][CH:19]=2)[CH:15]=[CH:16]1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 59214292HCID 59214292, compound

Product 1

HCID 59214290HCID 59214290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
52.5 °C

Procedure

To a solution of 4-{5-[4-fluoro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole (300 mg) in THF (1.5 ml) was added, propane-2-amine (0.75 ml), and after sealing the tube, the solution was stirred at 50 to 55° C. for 40 hours. It was concentrated under reduced pressure, and then purified by silica gel chromatography (n-hexane:EtOAc). The obtained solid was dissolved in acetone under heating, and added with n-hexane, and the precipitate was filtered to obtain 4-[3-(1H-indol-4-yl)-1,2,4-oxadiazol-5-yl]-N-isopropyl-2-(trifluoromethyl)aniline (295 mg).

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. custompurified by silica gel chromatography (n-hexane:EtOAc)
  3. dissolutionThe obtained solid was dissolved in acetone
  4. temperatureunder heating
  5. additionadded with n-hexane
  6. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-1e04bb612f7642b594af65da1e5446b1
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

Loading…