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

HRID 459753
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 459753
[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b55fb1327b13435bb8258b2a9cbf2499
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07196085B2

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