1,2-Dichloro-3-isocyanatobenzene → 3,5-Dichloro-N-(3-((3-(2,3-dichlorophenyl)-1-isobutylureido)methyl)benzyl)-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxybenzenesulfonamide

HRID 1889683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1889683
[Cl:1][C:2]1[C:3]([OH:40])=[C:4]([S:9]([N:12]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:41][C:42]1[C:47]([Cl:48])=[CH:46][CH:45]=[CH:44][C:43]=1[N:49]=[C:50]=[O:51]>C1COCC1>[Cl:1][C:2]1[C:3]([OH:40])=[C:4]([S:9]([N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:50]([NH:49][C:43]3[CH:44]=[CH:45][CH:46]=[C:47]([Cl:48])[C:42]=3[Cl:41])=[O:51])[CH:15]=2)[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)=[CH:29][CH:28]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

4

Edukt 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 585313773,5-Dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxy-N-(3-((isobutyl amino)methyl)benzyl)benzene sulfonamide2×

Produkt 1

HCID 666167203,5-Dichloro-N-(3-((3-(2,3-dichlorophenyl)-1-isobutylureido)methyl)benzyl)-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxybenzenesulfonamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3,5-dichloro-N-((4′-fluorobiphenyl-4-yl)methyl)-2-hydroxy-N-(3-((isobutyl amino)methyl)benzyl)benzene sulfonamide (Compound E of Example 184, 0.04 g, 0.0667 wool, 1.0 eq) in 25 mL of dry THF at 0° C. was added 2,3-dichlorophenyl isocyanate (0.012 g, 0.0667 mmol, 1.0 eq). The reaction mixture was stirred at ambient temperature for 15 min and concentrated. The residue was purified by preparative HPLC to afford the title compound (0.02 g, 40%). 1H NMR (400 MHz, DMSO-d6) δ 0.85-0.87 (d, 6H), 2.0 (m, 1H), 3.09-3.11 (d, 2H), 4.44-4.46 (m, 3H), 4.49 (s, 4H), 7.03-7.05 (d, 2H), 7.13-7.15 (d, 3H), 7.21-7.29 (m, 4H), 7.33-7.35 (m, 1H), 7.43-7.45 (d, 2H), 7.56-7.62 (m, 4H), 7.80 (s, 1H), 8.00 (s, 1H). MS (EP: 788.0 (M−H)−.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-70d097fdc19e4a57b0ac8d59b1f7d974
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501992B2

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