Triethylamine → HCID 71271075, Verbindung

HRID 1525857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525857
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]([NH2:11])=[O:10])=[C:4]([F:13])[CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.Cl.[CH:27]1([N:30]2[CH2:35][C:34]3([CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[O:33][CH2:32][C:31]2=[O:41])[CH2:29][CH2:28]1>C(#N)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:38]2[CH2:39][CH2:40][C:34]3([O:33][CH2:32][C:31](=[O:41])[N:30]([CH:27]4[CH2:28][CH2:29]4)[CH2:35]3)[CH2:36][CH2:37]2)[C:9]([NH2:11])=[O:10])=[C:4]([F:13])[CH:3]=1

Komponenten

7

Edukt 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 62225649HCID 62225649, VerbindungHCID 69083351HCID 69083351, Verbindung

Produkt 1

HCID 71271075HCID 71271075, VerbindungAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-bromo-2-fluorophenyl)-2-hydroxyacetamide (14.35 mmol) and triethylamine (43.1 mmol) in anhydrous acetonitrile (50.0 ml) was added neat methanesulfonyl chloride (20.81 mmol). The reaction stirred at room temperature for 18 hours then additional triethylamine (43.1 mmol) was added followed by solid 4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (15.79 mmol) in one portion. The reaction was heated at 90° C. for 3 hours then cooled to room temperature, diluted with water (150 mL) and stirred for 1 hour. The solids were collected by filtration, rinsed with water, and then dried by air suction and then vacuum to afford the title compound (3.53 g, 55% yield) as a white solid. MS(ES)+ m/e 440.1, 442.3 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction was heated at 90° C. for 3 hours
  2. temperaturethen cooled to room temperature
  3. stirringstirred for 1 hour
  4. filtrationThe solids were collected by filtration
  5. washrinsed with water
  6. customdried by air suction

Quellen und Nachweise

ORD-Eintrag
ord-8ddd97f39d4d44ac909806eb9e05c10f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09084794B2

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