2-Phenyl-2-propylsuccinic acid → 1-[3-(4-Oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-phenyl-3-propylpyrrolidine-2,5-dione

HRID 459753Notes

Reaction equation

HRID 459753 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][N:7]=1.[C:20]1([C:26]([CH2:34][CH2:35][CH3:36])([CH2:30][C:31](O)=[O:32])[C:27](O)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[O:16]=[C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([CH2:5][C:4]2[CH:3]=[C:2]([N:1]3[C:31](=[O:32])[CH2:30][C:26]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)([CH2:34][CH2:35][CH3:36])[C:27]3=[O:28])[CH:19]=[CH:18][CH:17]=2)=[N:7][NH:8]1

Participants

4

Reactant 2

HCID 2359142-Phenyl-2-propylsuccinic acidHCID 184443754-(3-aminobenzyl)-2H-phthalazin-1-one

Product 1

HCID 184443401-[3-(4-Oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-phenyl-3-propylpyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
200 °C

Procedure

A stirred mixture of 4-(3-aminobenzyl)-2H-phthalazin-1-one (0.1 g, 0.4 mmol; prepared in a manner similar to that described in Example 1) and 2-phenyl-2-propylsuccinic acid (0.094 g, 0.4 mmol) was heated at 200° C. for 1.5 hours then it was allowed to stand at ambient temperature for 18 hours. Methanol (1 ml) was added, the mixture was heated under reflux for 5 minutes, then it was filtered and the collected solid was washed with hot methanol (3 ml). The combined filtrate and washings were concentrated in vacuo and the residue was triturated with water (5 ml). The resulting solid was collected by filtration and dried in vacuo to give 1-[3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-phenyl-3-propylpyrrolidine-2,5-dione (0.061 g) as a beige solid, 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 0.95 (t, 3H) (CH3), 1.25 (m, 2H) (—CH2CH2CH3), 2.1 (m, 2H) (—CH2CH2CH3), 3.3 (d, 2H) (ring CH2), 4.4 (s, 2H) (ArCH2—), 7.2 (d, 1H) (ArH), 7.3–7.65 (m, 8H) (8×ArH), 7.85–8.1 (m, 3H) (3×ArH), 8.35 (d, 1H) (ArH), 12.7 (s, 1H) (CONH); m/z (M+H)+. 452, 93.6% purity.

Workup

  1. customprepared in a manner similar to
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 5 minutes
  4. filtrationit was filtered
  5. washthe collected solid was washed with hot methanol (3 ml)
  6. concentrationThe combined filtrate and washings were concentrated in vacuo
  7. customthe residue was triturated with water (5 ml)
  8. filtrationThe resulting solid was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b55fb1327b13435bb8258b2a9cbf2499
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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