N-Hydroxyphthalimide → HCID 68539763, compound

HRID 1187424Notes

Reaction equation

HRID 1187424 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:40]1[C:44](=[O:45])[C:43]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]2[C:41]1=[O:50].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][N:40]3[C:44](=[O:45])[C:43]4[C:42](=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:41]3=[O:50])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68538661HCID 68538661, compound

Product 1

HCID 68539763HCID 68539763, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cloudy solution of 4-(4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (1.0 g, 3.8 mmol), triphenylphosphine (1.49 g, 5.7 mmol) and N-hydroxyphthalimide (0.93 g, 5.7 mmol) in tetrahydrofuran (50 mL) was cooled to approximately 0° C.; then diisopropyl azodicarboxylate (1.33 mL, 6.8 mmol) was added dropwise. The reaction was allowed to warm to ambient temperature and was stirred for 5 hours. The solvent was removed under reduced pressure, and the resulting solid was purified by chromatography on silica gel (gradient elution with 0-10% methanol in dichloromethane with a small amount of concentrated ammonium hydroxide added) to provide 600 mg of 2-[4-(4amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butoxy]-1H-isoindole-1,3(2H)-dione as a yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting solid was purified by chromatography on silica gel (
  3. washgradient elution with 0-10% methanol in dichloromethane with a small amount of concentrated ammonium hydroxide
  4. additionadded)

Sources & evidence

ORD record
ord-9db92979bed54d15afe52d8e01475f4f
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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