Triethylamine → 3'-chloro-4-(5-methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

HRID 220554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220554
Cl.Cl.[Cl:3][C:4]1[C:5]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][N:9]=1.[CH3:16][C:17]1[N:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:20]=[CH:19][C:18]=1[CH:28]=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[Cl:3][C:4]1[C:5]([N:10]2[CH2:11][CH2:12][N:13]([CH2:28][C:18]3[CH:19]=[N:20][N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:17]=3[CH3:16])[CH2:14][CH2:15]2)=[N:6][CH:7]=[CH:8][N:9]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 27764375-Methyl-1-phenyl-1H-pyrazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 866416583'-chloro-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl dihydrochloride

Produkt 1

HCID 866416633'-chloro-4-(5-methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinylAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Dissolve 3′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl dihydrochloride (0.500 g, 1.84 mmol) in 1,2-dichloroethane (19 mL). Add 5-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (0.396 g, 2.13 mmol), triethylamine (594 μL, 4.26 mmol), sodium triacetoxyborohydride (0.677 g, 3.20 mmol) and acetic acid (200 μL) and stir at room temperature for 18 hr. Add aq. saturated sodium bicarbonate and extract four times with DCM. Dry combined organic layers (magnesium sulfate), filter, concentrate, and purify (silica gel chromatography, eluting with 0:100 to 100:0 ethyl acetate:hexanes) to give 3′-chloro-4-(5-methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (597 mg, 88%) MS (ES): m/z=369[M+H]+.

Aufarbeitung

  1. extractionAdd aq. saturated sodium bicarbonate and extract four times with DCM
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 0:100 to 100:0 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-61c365f268f544f988d355334b7c713b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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