Diisopropylethylamine → HCID 59451431, Verbindung

HRID 1875015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875015
[NH2:1][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]2[C:23]=1[CH:24]=[C:25]([C:32](Cl)=[O:33])[NH:26]2.C(N(C(C)C)CC)(C)C>ClCCl.O>[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]2[C:23]=1[CH:24]=[C:25]([C:32]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]3[CH:12]=[C:13]([C:14]#[N:15])[CH:16]=[C:17]([Cl:19])[CH:18]=3)[C:4]=1[F:20])=[O:33])[NH:26]2

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 28007564,6-dichloro-1H-indole-2-carbonyl chlorideHCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Produkt 1

HCID 59451431HCID 59451431, VerbindungAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.050 g, 0.16 mmol) in dichloromethane (1.5 mL) was added 4,6-dichloro-1H-indole-2-carbonyl chloride (0.060 g, 0.24 mmol) and diisopropylethylamine (0.031 g, 0.24 mmol). The resulting suspension was stirred at RT for 45 min. The reaction mixture was diluted with dichloromethane and water. A solid precipitated which was filtered and dried under vacuum to give the title compound (0.069 g, 82%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.12 (br. s., 1H), 9.20 (br. s., 1H), 7.77-7.78 (m, 1H), 7.41-7.52 (m, 3H), 7.33-7.41 (m, 2H), 7.23-7.32 (m, 1H), 7.19-7.20 (m, 1H), 4.54 (s, 2H). ES-LCMS: m/z 522 (M−H).

Aufarbeitung

  1. customA solid precipitated which
  2. filtrationwas filtered
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f224d5f9c6d8439c88dfb3ee7aa25174
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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