Hydrochloric Acid → N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-N'-(4-phenoxybutyl)succinamide

HRID 1797322

Reaktionsgleichung

Reaktionsgleichung von HRID 1797322
[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[Cl:19][C:20]1[CH:21]=[C:22]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[NH:42][C:43](=[O:49])[CH2:44][CH2:45][C:46](O)=[O:47])[CH:23]=[CH:24][C:25]=1[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33].[O:50]([CH2:57][CH2:58][CH2:59][CH2:60][NH2:61])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.Cl>CO>[Cl:19][C:20]1[CH:21]=[C:22]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[NH:42][C:43](=[O:49])[CH2:44][CH2:45][C:46]([NH:61][CH2:60][CH2:59][CH2:58][CH2:57][O:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:47])[CH:23]=[CH:24][C:25]=1[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1162404-Phenoxybutan-1-amineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 9845903N-[2-[3-Chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]-succinamic Acid

Produkt 1

HCID 22174446N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-N'-(4-phenoxybutyl)succinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride (DMT-MM) (69 mg, 0.25 mmol) was added to a solution of N-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid (100 mg, 0.23 mmol) (disclosed in WO 01/05746) and 4-phenoxybutylamine (30 mg, 0.25 mmol) in methanol (2.0 mL). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into 1 N HCl (aq.) and was extracted with EtOAc (×2). The combined organic phases were washed with water, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using DCM/MeOH/NH3(aq.) 95:5:0.5 as the eluent to afford the title compound as a yellow solid.

Aufarbeitung

  1. extractionwas extracted with EtOAc (×2)
  2. washThe combined organic phases were washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a5b9921d0e114ce1a50824a85c07b32b
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034015B2

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