2-Methoxyphenylboronic acid → 5-(5-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-2-(2-methoxy-phenyl)-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2204367
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:11]([C:14]3[CH:19]=[C:18]([Cl:20])[C:17](=[O:21])[N:16]([CH3:22])[CH:15]=3)[C:12](=[O:13])[C:4]=2[CH:3]=1.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O.BrC1N(C(C)C)C2C(C3C=CC(Cl)=CC=3)N(C3C=C(Cl)C=CC=3C)C(=O)C=2C=1.C(C1C=CC(OC)=C(B(O)O)C=1)#N>>[Cl:20][C:18]1[C:17](=[O:21])[N:16]([CH3:22])[CH:15]=[C:14]([N:11]2[C:12](=[O:13])[C:4]3[CH:3]=[C:2]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[O:31][CH3:30])[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]=3[CH:10]2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:19]=1

Komponenten

5

Edukt 4

HCID 27339582-Methoxyphenylboronic acidHCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic AcidHCID 867031442-bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one2×HCID 867031692-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Produkt 1

HCID 722042065-(5-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-2-(2-methoxy-phenyl)-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Versuchsvorschrift

The title compound was prepared in analogy to the procedure described for Example 17 but 2-bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate E) and 2-methoxyphenylboronic acid were used instead of 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one and 5-cyano-2-methoxyphenylboronic acid respectively. The title compound was obtained as a white solid. tR: 7.13 min (HPLC 2); ESI-MS: tR=1.20 min, [M+H]+522/524/526 (LC-MS 1); TLC: Rf=0.35 (95:5 CH2Cl2/MeOH); 1H-NMR (d6-DMSO, 600 MHz): 7.91 (m, 1H), 7.88 (m, 1H), 7.44 (m, 1H), 7.43 (m, 2H), 7.33 (m, 2H), 7.25 (m, 1H), 7.11 (m, 1H), 7.02 (m, 1H), 6.34 (s, 1H), 6.21 (s, 1H), 3.92 (m, 1H), 3.74 (s, 3H), 3.44 (s, 3H), 1.33 (m, 3H), 0.39 (m, 3H).

Aufarbeitung

  1. customThe title compound was prepared in analogy to the procedure

Quellen und Nachweise

ORD-Eintrag
ord-ad6cff026408498a811153a289f39348
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365576B2

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