N-Hydroxyphthalimide → HCID 69192599, compound

HRID 1187405Notes

Reaction equation

HRID 1187405 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][C:16]1[N:21]2[N:22]=[N:23][N:24]=[C:20]2[C:19]2[N:25]=[C:26]([CH2:32][CH2:33][CH3:34])[N:27]([CH2:28][CH2:29][CH2:30][OH:31])[C:18]=2[C:17]=1[CH3:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:56]1[C:60](=[O:61])[C:59]2=[CH:62][CH:63]=[CH:64][CH:65]=[C:58]2[C:57]1=[O:66]>CN(C=O)C>[CH3:15][C:16]1[N:21]2[N:22]=[N:23][N:24]=[C:20]2[C:19]2[N:25]=[C:26]([CH2:32][CH2:33][CH3:34])[N:27]([CH2:28][CH2:29][CH2:30][O:31][N:56]3[C:60](=[O:61])[C:59]4[C:58](=[CH:65][CH:64]=[CH:63][CH:62]=4)[C:57]3=[O:66])[C:18]=2[C:17]=1[CH3:35]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 69506319HCID 69506319, compound

Product 1

HCID 69192599HCID 69192599, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diisopropyl azodicarboxylate (372 μL, 1.89 mmol) was added to a stirred solution of 3-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)propan-1-ol (500 mg, 1.72 mmol), triphenylphosphine (496 mg, 1.89 mmol), and N-hydroxyphthalimide (308 mg, 1.89 mmol) in DMF (17 mL) at room temperature. After 4 hours, the solvent was removed under reduced pressure to afford an oil that was triturated with ethyl acetate to generate a pink solid. The solid was isolated by filtration and washed with ethyl acetate to yield 630 mg of 2-[3-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)propoxy]-1H-isoindole-1,3(2H)-dione as a pink powder.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customto afford an oil that
  3. customwas triturated with ethyl acetate
  4. customThe solid was isolated by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-d14eab403f7347459b3be36f3aeed7f0
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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