1,2-Dichloroethane → 1-{4-[4-(3-Methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-ethanone hydrochloride

HRID 220518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220518
[N:1]1([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=3)=[N:11][CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:22][C:23]1[C:27]([CH:28]=O)=[CH:26][N:25]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:50]CCCl>>[ClH:50].[CH3:22][C:23]1[C:27]([CH2:28][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[C:12]([C:13]4[CH:14]=[CH:15][C:16]([C:19](=[O:21])[CH3:20])=[CH:17][CH:18]=4)=[N:11][CH:10]=[CH:9][N:8]=3)[CH2:2][CH2:3]2)=[CH:26][N:25]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]=1

Komponenten

5

Edukt 4

HCID 111,2-DichloroethaneHCID 8488843-methyl-1-phenyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 685951741-[4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-ethanone

Produkt 1

HCID 685974181-{4-[4-(3-Methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-ethanone hydrochlorideAusbeute 18 %

Versuchsvorschrift

Dissolve 1-[4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-phenyl]-ethanone (0.5 g, 1.77 mmol) in 1,2 dichloroethane (4 mL). Add 3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (1.5 eq., 0.495 g, 2.66 mmol). Stir for 30 min. Add sodium triacetoxyborohydride (2.0 eq., 0.75 g, 3.54 mmol). Stir at room temperature for 48 hr. Purify by SCX column followed by normal phase chromatography with a gradient of 100% EtOAc-5% 7N NH3 in methanol/EtOAc to give the freebase of the title compound (0.15 g, 18% yield). MS (ES): m/z=453.2 [M+H]+. Dissolve (0.15 g, 0.33 mmol) in a mixture of acetonitrile (2 mL) and water (3 mL). Add aq. 1N HCl (1 eq., 0.33 mmol, 0.33 mL). Freeze the solution to −78° C. in a dry-ice/acetone bath. Place the solution in the lyophilizer for 48 hr. to give the title compound (0.156 g, 97% yield). MS (ES): m/z=453.2[M+H]+.

Aufarbeitung

  1. stirringStir at room temperature for 48 hr
  2. customPurify by SCX column

Quellen und Nachweise

ORD-Eintrag
ord-b76a6805d62044ef8c73ff57ab967bdb
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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