N-Hydroxyphthalimide → HCID 68534616, compound

HRID 1992614Notes

Reaction equation

HRID 1992614 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Br:15][C:16]1[CH:17]=[N:18][C:19]2[C:20]3[N:28]([CH2:29][CH2:30][CH2:31][OH:32])[C:27]([CH2:33][O:34][CH2:35][CH3:36])=[N:26][C:21]=3[CH:22]=[N:23][C:24]=2[CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:57]1[C:61](=[O:62])[C:60]2=[CH:63][CH:64]=[CH:65][CH:66]=[C:59]2[C:58]1=[O:67]>CN(C=O)C.C(OCC)(=O)C>[Br:15][C:16]1[CH:17]=[N:18][C:19]2[C:20]3[N:28]([CH2:29][CH2:30][CH2:31][O:32][N:57]4[C:61](=[O:62])[C:60]5[C:59](=[CH:66][CH:65]=[CH:64][CH:63]=5)[C:58]4=[O:67])[C:27]([CH2:33][O:34][CH2:35][CH3:36])=[N:26][C:21]=3[CH:22]=[N:23][C:24]=2[CH:25]=1

Participants

7

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68536752HCID 68536752, compound

Product 1

HCID 68534616HCID 68534616, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropyl azodicarboxylate (6.47 mL, 32.9 mmol) was added dropwise over ten minutes to a stirred solution of 3-[7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propan-1-ol (10.0 g, 27.4 mmol), triphenylphosphine (8.62 g, 32.9 mmol), and N-hydroxyphthalimide (5.36 g, 32.9 mmol) in DMF (110 mL) at 0° C. The reaction was allowed to warm to room temperature and was stirred overnight. The solvent was removed under reduced pressure to afford a solid that was slurried in ethyl acetate, isolated by filtration, washed with ethyl acetate, and dried under vacuum to yield 11.45 g of 2-{3-[7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propoxy}-1H-isoindole-1,3(2H)-dione as a pink solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto afford a solid
  3. customisolated by filtration
  4. washwashed with ethyl acetate
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4e396a701ef7442eb6f6bb5b9376adcc
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

Loading…