Triethylamine → HCID 21947944, Verbindung

HRID 2215141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215141
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19].S(Cl)(Cl)=O.[CH:24]1[CH:25]=[CH:26][N:27]2[CH2:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[NH:30][CH2:29][C:28]=12.C(N(CC)CC)C>O1CCCC1.ClCCl.CN(C)C=O>[Cl:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:8]([N:30]2[C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[CH2:33][N:27]3[CH:26]=[CH:25][CH:24]=[C:28]3[CH2:29]2)=[O:10])[CH:7]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 21947829HCID 21947829, Verbindung

Produkt 1

HCID 21947944HCID 21947944, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 2-chloro-2′-fluoro-5-methoxy[1,1′-biphenyl]-4-carboxylic acid of Step A (3.80 g, 13.5 mmol) in tetrahydrofuran (20 mL) containing a catalytic amount of N,N-dimethylformamide was added dropwise thionyl chloride (1.77 g, 14.9 mmol). The reaction mixture was stirred for 2 hours, and then added dropwise to a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (2.49 g, 13.5 mmol) in tetrahydrofuran (20 mL) containing triethylamine (3.0 g, 29.8 mmol). The reaction mixture was stirred for 2 hours, diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. Recrystallization of the residue from ethyl acetate/heptane provided the title compound as a pale yellow solid, m.p. 192–194° C., found to be 99.99% pure by analytical HPLC [Primesphere C-18 column (2.0×150 mm); mobile phase: gradientfrom 10 to 100% of acetonitrile/water containing 0.1% phosphoric acid, 7 minute gradient].

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 2 hours
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customRecrystallization of the residue from ethyl acetate/heptane

Quellen und Nachweise

ORD-Eintrag
ord-90310dba2bb540c1958d5dca656f8035
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109193B2

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