N-vinyl-2-pyrrolidone → 3-Chloro-8-methoxy-7-[1-(2-oxopyrrolidin-1-yl)vinyl]-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one

HRID 272740

Reaktionsgleichung

Reaktionsgleichung von HRID 272740
FC(F)(F)S(O[C:7]1[C:23]([O:24][CH3:25])=[CH:22][C:10]2[NH:11][C:12](=[O:21])[C:13]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:14]=3[NH:15][C:9]=2[CH:8]=1)(=O)=O.[CH:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1=[O:35])=[CH2:29].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:13]2[C:12](=[O:21])[NH:11][C:10]3[CH:22]=[C:23]([O:24][CH3:25])[C:7]([C:28]([N:30]4[CH2:34][CH2:33][CH2:32][C:31]4=[O:35])=[CH2:29])=[CH:8][C:9]=3[NH:15][C:14]=2[CH:16]=1

Komponenten

7

Edukt 3

HCID 6917N-vinyl-2-pyrrolidoneHCID 8471TriethylamineHCID 877382003-chloro-8-methoxy-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-7-yl trifluoromethanesulfonate

Produkt 1

HCID 692177743-Chloro-8-methoxy-7-[1-(2-oxopyrrolidin-1-yl)vinyl]-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of Example 516A, 1-vinyl-2-pyrrolidinone, Pd(dppf)Cl2-CH2Cl2, and triethylamine in DMF was heated at 110° C. overnight, cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel using a solvent gradient that increased from 1 to 4% methanol in dichloromethane to give the title compound. MS (ESI) m/e 384 (M+H)+.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by column chromatography on silica gel using a solvent gradient that
  6. temperatureincreased from 1 to 4% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-ef4269893cc14acf92ab779d66eb474b
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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