Triethylamine → 1-[4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-1-piperazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

HRID 238664

Reaktionsgleichung

Reaktionsgleichung von HRID 238664
Cl.[C:2]1([CH:8]2[O:12][N:11]=[C:10]([C:13]3[N:14]=[C:15]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[S:16][CH:17]=3)[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][C:25]1[N:29]([CH2:30][C:31](O)=[O:32])[N:28]=[C:27]([C:34]([F:37])([F:36])[F:35])[CH:26]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1>ClCCl>[C:2]1([CH:8]2[O:12][N:11]=[C:10]([C:13]3[N:14]=[C:15]([N:18]4[CH2:23][CH2:22][N:21]([C:31](=[O:32])[CH2:30][N:29]5[C:25]([CH3:24])=[CH:26][C:27]([C:34]([F:37])([F:36])[F:35])=[N:28]5)[CH2:20][CH2:19]4)[S:16][CH:17]=3)[CH2:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 5961182-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 672350611-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]piperazine hydrochloride2×

Produkt 1

HCID 687468181-[4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-1-piperazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]piperazine hydrochloride (i.e. the product of Example 7, Step E) (200 mg, 0.57 mmol) and 5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-acetic acid (0.120 g, 0.57 mmol) in dichloromethane (10 mL) at room temperature was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.110 g, 0.57 mmol), triethylamine (0.086 g, 0.85 mmol) and 1-hydroxy-benzotriazole hydrate (0.020 g, 0.14 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with dichloromethane (30 mL), and washed with water (20 mL) and brine (20 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude residue was purified by column chromatography using 3% methanol in chloroform as eluant to give 180 mg of the title product, a compound of the present invention as a white solid.

Aufarbeitung

  1. washwashed with water (20 mL) and brine (20 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-84e46a130f364cb28bb30fab0e72b687
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642634B2

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