Hydrochloric Acid → HCID 86601236, Verbindung

HRID 349283

Reaktionsgleichung

Reaktionsgleichung von HRID 349283
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.CON(C)[C:21]([C:23]1[N:24]=[N:25][N:26]([CH2:34][C:35]2[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([C:45]([F:48])([F:47])[F:46])[CH:36]=2)[C:27]=1[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=[O:22].Cl>C1COCC1.CCOCC.CCOC(C)=O>[F:44][C:41]([F:42])([F:43])[C:39]1[CH:40]=[C:35]([CH:36]=[C:37]([C:45]([F:46])([F:48])[F:47])[CH:38]=1)[CH2:34][N:26]1[C:27]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[C:23]([C:21]([C:14]2[N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[Cl:6])[CH:17]=[CH:16][N:15]=2)=[O:22])[N:24]=[N:25]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 1428581-(2-Chlorophenyl)imidazoleHCID 866012371-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid methoxy-methyl-amideHCID 178418339Butyllithium

Produkt 1

HCID 86601236HCID 86601236, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Add BuLi (0.80 mL, 1.28 mmol) to a −78° C. solution of 1-(2-chloro-phenyl)-1H-imidazole (200 mg, 1.12 mmol) in THF (3 mL). Stir at −78° C. for 20 min., then add a solution of 1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid methoxy-methyl-amide (261 mg, 0.57 mmol) in THF (2 mL) via cannula. Stir the resulting solution at −78° C. for 10 min., then allow to warm to RT and stir for 2 h. Add 1N HCl (1.3 mL) and stir for 30 min. Dilute reaction with EtOAc (50 mL) and wash with water (20 mL), saturated NaHCO3 (20 mL) and brine (20 mL). Dry, filter and concentrate the organic solution and purify the crude material by silica gel chromatography (20% to 80% EtOAc/hexanes) to give a brown solid. Trituration with cold ether gives the title compound as a fine white powder. MS [ES] 577.2 (M+H)+. 1H NMR (400 MHz, CHCl3) δ 8.68 (dd, 1H, J=1.4, 4.8 Hz), 8.48 (d, 1H, J=1.8 Hz), 7.81 (s, 1H), 7.48 (m, 3H), 7.46 (m, 1H), 7.44 (m, 1H), 7.34 (m, 4H), 7.17 (m, 1H), 5.60 (s, 2H).

Aufarbeitung

  1. stirringStir the resulting solution at −78° C. for 10 min.
  2. temperatureto warm to RT
  3. stirringstir for 2 h
  4. stirringstir for 30 min
  5. additionDilute
  6. washwash with water (20 mL), saturated NaHCO3 (20 mL) and brine (20 mL)
  7. customDry
  8. filtrationfilter
  9. concentrationconcentrate the organic solution
  10. custompurify the crude material by silica gel chromatography (20% to 80% EtOAc/hexanes)
  11. customto give a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-fd6e3dac755b431cba76f693c92ff06f
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179804B2

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