Sodium hydride → [6-(3-Chloro-[1,2,4]triazol-1-yl)-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517088
[Cl:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[H-].[Na+].Cl[C:10]1[N:15]=[C:14]([C:16]([N:18]2[CH2:23][CH2:22][CH:21]([N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:20][CH2:19]2)=[O:17])[C:13]([CH3:29])=[CH:12][C:11]=1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=1>CN1CCCC1=O>[Cl:1][C:2]1[N:6]=[CH:5][N:4]([C:10]2[N:15]=[C:14]([C:16]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:25][CH2:26][CH2:27][CH2:28]4)[CH2:20][CH2:19]3)=[O:17])[C:13]([CH3:29])=[CH:12][C:11]=2[C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:38])([F:39])[F:37])[CH:31]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 44547211[6-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneHCID 178478410HCID 178478410, Verbindung

Produkt 1

HCID 58016727[6-(3-Chloro-[1,2,4]triazol-1-yl)-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A well stirred solution of 0.17 g (1.59 mmol) of 3-chloro-1H-[1,2,4]triazole in 1.0 ml of 1-methyl-pyrrolidin-2-one was treated at RT with 0.058 g (1.32 mmol) of a sodium hydride (55% in mineral oil). After 30 min, 0.20 g (0.44 mmol) of [6-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 3) was added and the reaction mixture was heated up to 150° C. After 24 hours, it was poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5) to give 0.11 g (48%) of the title compound as yellow oil. MS: 519.3 (MH+, 1Cl).

Aufarbeitung

  1. waitAfter 24 hours
  2. additionit was poured
  3. extractionextracted twice with EtOAc
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-51a50c7bdf1146b5a825dadbb133dee8
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227613B2

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