2-(3-azidopropyl)-2,3-dihydro-1H-isoindole-1,3-dione → 2-{3-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)-[1,2,3]triazol-1-yl]-propyl)-isoindole-1,3-dione

HRID 1767042Notes

Reaction equation

HRID 1767042 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2)#[CH:2].[N:15]([CH2:18][CH2:19][CH2:20][N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31])=[N+:16]=[N-:17]>C1(C)C=CC=CC=1>[CH3:14][O:13][C:10]1[N:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[CH:5][CH:4]=[C:3]2[C:1]1[N:17]=[N:16][N:15]([CH2:18][CH2:19][CH2:20][N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])[CH:2]=1

Participants

4

Reactant 2

HCID 1864562-(3-azidopropyl)-2,3-dihydro-1H-isoindole-1,3-dioneHCID 21113160HCID 21113160, compound

Product 1

HCID 211131512-{3-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)-[1,2,3]triazol-1-yl]-propyl)-isoindole-1,3-dioneYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 8-ethynyl-2-methoxy-[1,5]naphthyridine (184 mg, 1.0 mmlole) and 2-(3-azido-propyl)-isoindole-1,3-dione (230 mg, 1.0 mmole) were refluxed in toluene (5 mL) for 12 hours. Upon cooling the product precipitated. The mixture was diluted with ether (5 mL) filtered, and the solid product was washed with ether and dried to give 190 mg (46%) of 2-{3-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)-[1,2,3]triazol-1-yl]-propyl}-isoindole-1,3-dione as a grey solid as single regioisomer.

Workup

  1. temperatureUpon cooling the product
  2. customprecipitated
  3. additionThe mixture was diluted with ether (5 mL)
  4. filtrationfiltered
  5. washthe solid product was washed with ether
  6. customdried

Sources & evidence

ORD record
ord-34abef989e5a42c3a79b2bde5d0ee3f2
Source dataset
uspto-grants-2007_06
Patent number
US07232832B2

Reaction notes

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