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

HRID 2354332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354332
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][CH3:16])[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[Cl:28])[N:24]([CH2:29][C:30]([OH:32])=O)[C:23](=[O:33])[CH2:22]C2.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>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:15]([CH3:16])[C:30](=[O:32])[CH2:29][N:24]2[C:25]3[CH:26]=[C:27]([Cl:28])[C:18]([Cl:17])=[CH:19][C:20]=3[O:44][CH2:22][C:23]2=[O:33])[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57418662(6,7-dichloro-2-oxo-3,4-dihydro-1(2H)-quinolinyl)acetic acidHCID 57425537[1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethyl]methylamine

Produkt 1

HCID 57488849N-[1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamideAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of [1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethyl]methylamine (1.61 g, 5.68 mmol) and (6,7-dichloro-2-oxo-3,4-dihydro-1(2H)-quinolinyl)acetic acid (1.73 g, 6.25 mmol) in DMF (20 mL) was added BOP Reagent (3.77 g, 8.52 mmol) and triethylamine (1.72 g, 17.3 mmol). The resultant mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduce pressure. The residue was diluted with ethyl acetate (100 mL) and extracted with 5% NaHCO3 (100 mL) and brine (100 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (120 g redisep column, silica 40 um, 60 A, 85 ml/min, A: MeOH, B: CH2Cl2, A: 1% for 20 min) to give 0.76 g (25%) title compound as yellow solid. MS (ES) m/e 545.4 [M+H]+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additionThe residue was diluted with ethyl acetate (100 mL)
  3. extractionextracted with 5% NaHCO3 (100 mL) and brine (100 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (120 g redisep column, silica 40 um, 60 A, 85 ml/min

Quellen und Nachweise

ORD-Eintrag
ord-2d38b5ae9433436faaf6a2b41ec00005
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749998B2

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