Phthalimide → HCID 57593205, compound

HRID 1784466Notes

Reaction equation

HRID 1784466 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]2=[N:10][C:9]=1[CH:19](O)[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]2=[N:10][C:9]=1[CH:19]([N:28]1[C:24](=[O:34])[C:25]2[C:26](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:27]1=[O:29])[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57593199HCID 57593199, compound

Product 1

HCID 57593205HCID 57593205, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A previous batch of the product from Step 8 (18) was combined with the above and 150 mg (0.48 mmol) of this crude material was dissolved in 3 ml of dry tetrahydrofuran then cooled to 0° C. Phthalimide 212 mg (1.4 mmol) was added to the cold solution followed by triphenylphosphine 189 mg (0.72 mmol) then DIAD 140 μl (0.72 mmol). The reaction mixture was stirred under nitrogen and allowed to warm to room temperature overnight. The solvent was evaporated and the solid redissolved in ethyl acetate then washed with saturated NaHCO3 and brine. The organic layer was then dried over MgSO4 and the solvent was removed in vacuo resulting in 700 mg of crude material that was purified by flash chromatography to give 95 mg (0.22 mmol, 44%) of 2-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-1H-isoindole-1,3(2H)-dione (19) as a white solid.

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe solvent was evaporated
  3. dissolutionthe solid redissolved in ethyl acetate
  4. washthen washed with saturated NaHCO3 and brine
  5. dry with materialThe organic layer was then dried over MgSO4
  6. customthe solvent was removed in vacuo
  7. customresulting in 700 mg of crude material that
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-abdcff8565974421a008799f7eedc0ca
Source dataset
uspto-grants-2009_03
Patent number
US07504405B2

Reaction notes

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