(4-Tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine → N-(4-tert-butylbenzyl)-2-chloro-N-[2-(3,4-dichlorophenyl)-ethyl]-3-fluoro-6-methylaminobenzamide

HRID 2244378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244378
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])OC(=O)[N:7]([CH3:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:15].[C:16]([C:20]1[CH:37]=[CH:36][C:23]([CH2:24][NH:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.C(OCC)(=O)C>[C:16]([C:20]1[CH:37]=[CH:36][C:23]([CH2:24][N:25]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[C:10](=[O:12])[C:11]2[C:6]([NH:7][CH3:14])=[CH:5][CH:4]=[C:3]([F:15])[C:2]=2[Cl:1])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Komponenten

5

Edukt 2

HCID 68563688(4-Tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amineHCID 866152375-chloro-6-fluoro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

Produkt 1

HCID 68699593N-(4-tert-butylbenzyl)-2-chloro-N-[2-(3,4-dichlorophenyl)-ethyl]-3-fluoro-6-methylaminobenzamideAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 5-chloro-6-fluoro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (83 mg, 0.36 mmol) and (4-tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine (122 mg, 0.36 mmol) in DMF (2 ml) was heated to 140° C. for 2 h and then at 110° C. overnight. The reaction mixture was then cooled to RT and the mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography to give the desired product (51 mg, 27%) as a white solid. MS (ISP) 521.9 (M+H)+.

Aufarbeitung

  1. customat 110° C.
  2. customovernight
  3. temperatureThe reaction mixture was then cooled to RT
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue which
  9. customwas purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-852e110b28ee4bfc94e3a55108dd8d44
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678818B2

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