Diisopropylethylamine → 2-Bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-ethyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2204310
[Br:1][C:2]1[N:6]([CH2:7][CH3:8])[C:5]([CH:9]([NH:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[CH3:25])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:4]([C:26](O)=[O:27])[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>O>[Br:1][C:2]1[N:6]([CH2:7][CH3:8])[C:5]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[N:17]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[CH3:25])[C:26](=[O:27])[C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 867031155-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid

Produkt 1

HCID 867031142-Bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-ethyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid (Step K1) (3.11 mmol), TBTU (4.36 mmol) and DIEA (9.33 mmol) was stirred at 80° C. for 1 h. The reaction mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were washed successively with H2O and brine, dried (MgSO4), filtered and concentrated. The product was purified by chromatography column to afford the title compound as a colorless oil. tR: 5.90 min (HPLC 4); ESI-MS: tR=1.35 min, [M+H]+ not ionized (LC-MS 1).

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed successively with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by chromatography column

Quellen und Nachweise

ORD-Eintrag
ord-b6c5cb40b4904a68bfb17da43280dfd8
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365576B2

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