Triethylamine → N-[1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide

HRID 2354343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354343
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:16][CH3:17])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.[Cl:18][C:19]1[C:20]([Cl:33])=[CH:21][C:22]2[O:27][CH2:26][CH2:25][N:24]([CH2:28][C:29]([OH:31])=O)[C:23]=2[CH:32]=1.CN([P+]([O:44]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([N:16]([CH3:17])[C:29](=[O:31])[CH2:28][N:24]2[C:23]3[CH:32]=[C:19]([Cl:18])[C:20]([Cl:33])=[CH:21][C:22]=3[O:27][CH2:26][C:25]2=[O:44])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57418663HCID 57418663, VerbindungHCID 57501274[1-(3-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine

Produkt 1

HCID 57457162N-[1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamideAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of [1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]methylamine (3.06 g, 10.2 mmol) and (6,7-dichloro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetic acid (2.82 g, 10.2 mmol) was dissolved in a mixture of dichloromethane and DMF (1:1, 100 mL). BOP Reagent (7.16 g, 16.6 mmol) was added followed by triethylamine (4.36 g, 43.2 mmol). The resultant mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL) and extracted with 5% NaHCO3 (150 mL) and brine (150 mL). The organic layer was dried over MgSO4, and concentrated. The residue was recrystallized in ether, and the crystal was collected by filtration to give the title compound as a white solid (3.17 g, 56%). MS (ESI): 556.2 [M+H]+.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  3. extractionextracted with 5% NaHCO3 (150 mL) and brine (150 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was recrystallized in ether
  7. filtrationthe crystal was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-fcfa6cf350a945eebe1e529df8cda757
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749998B2

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