1,2-Dichloroethane → ethyl 3-tert-butyl-1-(2-morpholino-2-oxoethyl)-1H-pyrazole-5-carboxylate

HRID 1930425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930425
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH2:15][C:16]([OH:18])=O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.Cl>CN(C=O)C.O>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH2:15][C:16]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:18])[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 206071732-(3-tert-butyl-5-(ethoxycarbonyl)-1H-pyrazol-1-yl)acetic acid

Produkt 1

HCID 69036388ethyl 3-tert-butyl-1-(2-morpholino-2-oxoethyl)-1H-pyrazole-5-carboxylateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-tert-butyl-5-(ethoxycarbonyl)-1H-pyrazol-1-yl)acetic acid from Example B17 (0.77 g, 3.02 mmol) in DMF (5 mL) were added EDC (0.75 g, 3.93 mmol), HOBt (0.55 g, 3.62 mmol) and morpholine (0.39 g, 4.53 mmol). After stirring the mixture for 4 h at RT, water (50 mL) and 3M HCl (5 mL) were added and the product was extracted with EtOAc (3×30 mL). The combined organic layers were washed with aq. LiCl, dried (Na2SO4), concentrated and purified by chromatography (EtOAc/CH2Cl2) to afford ethyl 3-tert-butyl-1-(2-morpholino-2-oxoethyl)-1H-pyrazole-5-carboxylate (0.67 g, 69% yield) as a solid. 1H NMR (400 MHz, Acetone-d6): δ 6.74 (s, 1H), 5.40 (s, 2H), 4.27 (q, J=7.2 Hz, 2H), 3.73 (brs, 2H), 3.65-3.62 (m, 4H), 3.51 (brs, 2H), 1.32 (t, J=7.2 Hz, 3H), 1.29 (s, 9H); MS (ESI) m/z: 324.2 (M+H+).

Aufarbeitung

  1. extractionthe product was extracted with EtOAc (3×30 mL)
  2. washThe combined organic layers were washed with aq. LiCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by chromatography (EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-ea3609b9da9d42e6be50c8230bd75732
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188113B2

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