Dibromomethane → 4-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-1-yl]-4H-1,2,4-triazol-3-ylthio)acetamido]-3-chlorobenzoic acid

HRID 425314

Reaktionsgleichung

Reaktionsgleichung von HRID 425314
ClC(Cl)C(O)=O.N[C:8]1[N:9]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=3)[C:31]([CH:40]3[CH2:42][CH2:41]3)=[CH:30][CH:29]=2)[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=2[Cl:27])=[O:16])=[N:11][N:12]=1.N([O-])=O.[Na+].[Br:47]CBr>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:47][C:8]1[N:9]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=3)[C:31]([CH:40]3[CH2:42][CH2:41]3)=[CH:30][CH:29]=2)[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=2[Cl:27])=[O:16])=[N:11][N:12]=1

Komponenten

6

Edukt 4

HCID 3024DibromomethaneHCID 6597Dichloroacetic AcidHCID 23668193Sodium NitriteHCID 598131054-[2-(5-amino-4-[4-cyclopropyl-7-methoxynaphthalen-1-yl]-4H-1,2,4-triazol-3-ylthio)acetamido]-3-chlorobenzoic acid

Produkt 1

HCID 162218174-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-1-yl]-4H-1,2,4-triazol-3-ylthio)acetamido]-3-chlorobenzoic acidAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 165294Benzyltriethylammonium bromideKatalysator

Versuchsvorschrift

Dichloroacetic acid (0.063 ml, 0.76 mmol) was added to a mixture of compound 12 (200 mg, 0.38 mmol), benzyltriethyl ammonium bromide (311 mg, 1.14 mmol) and sodium nitrite (526 mg, 7.63 mmol) in dibromomethane (3 mL). The mixture was stirred at room temperature for 18 hours in the dark. The reaction mixture was then concentrated and the resulting residue was purified by prep. TLC (95% dichloromethane/5% methanol) to afford 90.4 mg of 4-[2-(5-bromo-4-[4-cyclopropyl-7-methoxynaphthalen-1-yl]-4H-1,2,4-triazol-3-ylthio)acetamido]-3-chlorobenzoic acid (13), 40% yield.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. customthe resulting residue was purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-98db5c12691a46a7aa4fd7dd69a5de02
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106205B2

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