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Triethylamine hydrochloride → HCID 178521701, Verbindung

HRID 1409536
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1409536
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]2[N:12]([N:21]=[CH:22][C:23]=2[C:24](=[O:34])[NH:25][C:26]2([C:32]#[N:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.[N-:35]=[N+:36]=[N-:37].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]2[N:12]([N:21]=[CH:22][C:23]=2[C:24](=[O:34])[NH:25][C:26]2([C:32]3[NH:37][N:36]=[N:35][N:33]=3)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11130Triethylamine hydrochloride2×HCID 33557Sodium Azide2×HCID 24772730HCID 24772730, Verbindung

Produkt 1

HCID 178521701HCID 178521701, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of the compound obtained in Example A1 (106 mg) in toluene (4 mL) and dimethylformamide (1.5 mL) were added sodium azide (86 mg) and triethylamine hydrochloride (183 mg), and the mixture was stirred at 120° C. for 24 hours. To the reaction mixture were further added sodium azide (90 mg) and triethylamine hydrochloride (183 mg), and the mixture was stirred for 21 hours. After cooling to room temperature, the reaction mixture was filtered through Celite to remove precipitates, and the filtrate was concentrated in vacuo. The resultant crude product was purified successively by column chromatography on silica gel (solvent; chloroform/methanol=100/0 to 95/5) and gel-permeation chromatography (solvent; chloroform) to give 6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-[N-[1-(1,2,3,4-tetrazol-5-yl)cyclohexyl]carbamoyl]-pyrazolo[1,5-a]pyrimidine (95 mg, yield: 83%) as a powder.

Aufarbeitung

  1. stirringthe mixture was stirred for 21 hours
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtered through Celite
  4. customto remove
  5. customprecipitates
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resultant crude product was purified successively by column chromatography on silica gel (solvent; chloroform/methanol=100/0 to 95/5) and gel-permeation chromatography (solvent; chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-f90c999f245047a0a5d4c9ff67bf0200
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08921380B2

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