1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(4-(1,3-dioxolan-2-yl)phenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazole

HRID 1941887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1941887
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([OH:18])=O)[CH:9]=[N:8]1.CC[N:21]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[O:40]1[CH2:44][CH2:43][O:42][CH:41]1[C:45]1[CH:52]=[CH:51][C:48]([C:49]#[N:50])=[CH:47][CH:46]=1>CN(C=O)C>[O:40]1[CH2:44][CH2:43][O:42][CH:41]1[C:45]1[CH:52]=[CH:51][C:48]([C:49]2[N:21]=[C:16]([C:10]3[CH:9]=[N:8][N:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[C:11]=3[C:12]([F:13])([F:14])[F:15])[O:18][N:50]=2)=[CH:47][CH:46]=1

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27784284-(1,3-Dioxolan-2-yl)benzonitrileHCID 167877231-(2-Pyridinyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

Produkt 1

HCID 669966503-(4-(1,3-dioxolan-2-yl)phenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (31.46 g, 122 mmol) in DMF (200 mL) was added EDCI (23.34 g, 134 mmol) and HOBt (16.53 g, 122 mmol). After the reaction was stirred for 30 min. at room temperature 4-(1,3-dioxolan-2-yl)benzonitrile, Int.6-A, (16.53 g, 122 mmol) was added. The reaction mixture was stirred at 140° C. for 4 hr. The reaction mixture was concentrated under reduced pressure to remove the volatiles. The residue was partitioned between water and ethyl acetate and the organic layer was washed with aq. HCl solution, NaHCO3 solution, water, and brine before being dried over Na2SO4 and concentrated to provide 3-(4-(1,3-dioxolan-2-yl)phenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazole (25 g, 58 mmol). The compound had an HPLC retention time=6.15 min. −Column: HYPERSIL® BDS C18 (4.6×50 mm) Flow rate=0.8 mL/min. Solvent A=, 0.1% TFA in water; Solvent B=acetonitrile. 5%-100% B (0-6 min), 100% B (6-9 min), 100%-5% B (9-11 min). LC/MS M+1=430.0.

Aufarbeitung

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto remove the volatiles
  4. customThe residue was partitioned between water and ethyl acetate
  5. washthe organic layer was washed with aq. HCl solution, NaHCO3 solution, water, and brine
  6. dry with materialbefore being dried over Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-52e85c73cce64fa2971456a0772dae4b
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389509B2

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