Phosphorus oxychloride → 2-(3-(1-Chloro-8-methoxy-2,7-naphthyridin-3-yl)propyl)isoindoline-1,3-dione

HRID 1034941Notes

Reaction equation

HRID 1034941 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=O)[NH:10][C:9]([CH2:14][CH2:15][CH2:16][N:17]1[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]1=[O:27])=[CH:8]2.O=P(Cl)(Cl)[Cl:30]>CC#N>[Cl:30][C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[N:4][C:3]=2[O:2][CH3:1])[CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])[N:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 580946292-(3-(8-Methoxy-1-oxo-1,2-dihydro-2,7-naphthyridin-3-yl)propyl)isoindoline-1,3-dione

Product 1

HCID 580936562-(3-(1-Chloro-8-methoxy-2,7-naphthyridin-3-yl)propyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(3-(8-Methoxy-1-oxo-1,2-dihydro-2,7-naphthyridin-3-yl)propyl)isoindoline-1,3-dione (200 mg, 0.55 mmol) is dissolved in CH3CN (2 mL) and POCl3 (59 uL, 0.64 mmol) The mixture is stirred at 80° C. for 3 hours. POCl3 is removed and neutralized with sat. NaHCO3. The compound is extracted with CHCl3 and the organic layer is dried (Na2SO4) and evaporated to yield the crude compound, which is used in the next step without any further purification. MS m/z 382.1 (M+1).

Workup

  1. customPOCl3 is removed
  2. extractionThe compound is extracted with CHCl3
  3. dry with materialthe organic layer is dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-af7349c509ba4aadb9321168b6d9176d
Source dataset
uspto-grants-2013_10
Patent number
US08546370B2

Reaction notes

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