N-Hydroxyphthalimide → 2-[3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione

HRID 1187400Notes

Reaction equation

HRID 1187400 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[N:15]1([CH2:28][CH2:29][CH2:30][OH:31])[C:27]2[C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:17]=[CH:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:52]1[C:56](=[O:57])[C:55]2=[CH:58][CH:59]=[CH:60][CH:61]=[C:54]2[C:53]1=[O:62]>O1CCCC1>[N:15]1([CH2:28][CH2:29][CH2:30][O:31][N:52]2[C:56](=[O:57])[C:55]3[C:54](=[CH:61][CH:60]=[CH:59][CH:58]=3)[C:53]2=[O:62])[C:27]2[C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:17]=[CH:16]1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 69192521HCID 69192521, compound

Product 1

HCID 695062792-[3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dioneYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (1.01 mL, 6.05 mmol) was added dropwise to a stirred solution of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol (1.15 g, 5.04 mmol), triphenylphosphine (1.59 g, 6.05 mmol), and N-hydroxyphthalimide (0.986 g, 6.05 mmol) in tetrahydrofuran (25 mL) at 0° C. The reaction was allowed to warrn to room temperature and was stirred overnight. The product was isolated by filtration and washed with a minimal amount of tetrahydrofuran to afford 1.47 g of 2-[3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione as a pale yellow solid.

Workup

  1. customto warrn to room temperature
  2. customThe product was isolated by filtration
  3. washwashed with a minimal amount of tetrahydrofuran

Sources & evidence

ORD record
ord-4ac019e4981046eaaf097e7d327fa69f
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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