Isopropylamine → HCID 59214378, compound

HRID 2244643Notes

Reaction equation

HRID 2244643 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[CH:16]=[CH:17][N:18]4[CH2:23][C:24]([NH2:26])=[O:25])[N:10]=2)[CH:5]=[N:6][C:7]=1Cl.[CH:27]([NH2:30])([CH3:29])[CH3:28]>O1CCOCC1.CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[CH:16]=[CH:17][N:18]4[CH2:23][C:24]([NH2:26])=[O:25])[N:10]=2)[CH:5]=[N:6][C:7]=1[NH:30][CH:27]([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 59214214HCID 59214214, compound

Product 1

HCID 59214378HCID 59214378, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a mixed solution of 2-{4-[5-(5,6-dichloropyridin-3-yl)-1,2,4-oxadiazol-3-yl]-1H-indol-1-yl}acetamide (100 mg) in dioxane (2 ml) and NMP (2 ml) was added isopropylamine (220 μl), followed by stirring at 150° C. for 1 hour in a microwave reaction vessel. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by silica gel chromatography (n-hexane:EtOAc=40:60 to 0:100), and the obtained residue was suspended in diisopropyl ether under heating, and collected by filtration to obtain 2-(4-{5-[5-chloro-6-(isopropylamino)pyridin-3-yl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)acetamide (62 mg) as white powders.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (n-hexane:EtOAc=40:60 to 0:100)
  3. temperatureunder heating
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-52877ea2434c4a30843dee25c646a06d
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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