Hydrochloric Acid → 1-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)pyrrolidine-2,5-dione

HRID 1797318

Reaktionsgleichung

Reaktionsgleichung von HRID 1797318
C(OC(Cl)=O)C(C)C.[Cl:9][C:10]1[CH:11]=[C:12]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][C:33](=[O:39])[CH2:34][CH2:35][C:36]([OH:38])=O)[CH:13]=[CH:14][C:15]=1[C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23].CN1CCOCC1.C(N(C(C)C)C(C)C)C.Cl>C1COCC1.CCOC(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:32]2[C:36](=[O:38])[CH2:35][CH2:34][C:33]2=[O:39])[CH:13]=[CH:14][C:15]=1[C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 9845903N-[2-[3-Chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]-succinamic Acid

Produkt 1

HCID 221744561-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)pyrrolidine-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Iso-butylchloroformate (60 μL, 0.46 mmol) was added to a stirred solution of N-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid (200 mg, 0.46 mmol) (disclosed in WO 01/05746) and 4-methylmorpholine (51 μL, 0.46 mmol) in THF (5.0 mL) at −15° C. After 5 min at 0° C. the reaction mixture was cooled to −15° C. and a solution of ethyl diisopropyl amine (65 μL, 0.46 mmol) in THF (5.0 mL) was added. The resulting reaction mixture was kept at 0° C. for 1 h. The reaction mixture was stirred for 16 h at RT and then poured into a mixture of 1 M HCl(aq) and EtOAc. The organic phase was washed with more HCl(aq)(×2). The organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using petroleum ether/EtOAc 1:2 as the eluent to afford the title compound as an oil.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washThe organic phase was washed with more HCl(aq)(×2)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-76dee2b40dd6468d9a349eeade00fdd4
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034015B2

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