Triethylamine → 9-[4-(3-Chlorophenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1622812

Reaktionsgleichung

Reaktionsgleichung von HRID 1622812
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[O:11]=[S:12]1(=[O:29])[CH2:17][CH2:16][N:15]2[CH2:18][CH2:19][CH2:20][CH:21]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[C:14]2=[N:13]1.C(N(CC)CC)C>CC#N.C(O[Cu]OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:28][C:25]1[CH:24]=[CH:23][C:22]([CH:21]2[C:14]3=[N:13][S:12](=[O:29])(=[O:11])[CH2:17][CH2:16][N:15]3[CH2:18][CH2:19][CH2:20]2)=[CH:27][CH:26]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2734323(3-Chlorophenyl)boronic acidHCID 667477204-(2,2-Dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

Produkt 1

HCID 668237379-[4-(3-Chlorophenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideAusbeute 26,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178476681HCID 178476681, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 3-chlorophenylboronic acid (167 mg), 4-(2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (100 mg), diacetoxycopper (130 mg), triethylamine (0.248 mL), and powdered 4A MS (1.00 g) in MeCN (10 mL) was stirred at room temperature overnight. The mixture was added with NH silica gel, concentrated in vacuo, and purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc), and then recrystallized from EtOAc-IPE to give the title compound (37.0 mg) as a white solid.

Aufarbeitung

  1. additionThe mixture was added with NH silica gel
  2. concentrationconcentrated in vacuo
  3. custompurified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  4. customrecrystallized from EtOAc-IPE

Quellen und Nachweise

ORD-Eintrag
ord-63f7daeafcce40c38b80f0a124261db4
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778934B2

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