Acetic Acid → 3'-(4-Chlorophenyl)-4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine hydrochloride

HRID 220519

Reaktionsgleichung

Reaktionsgleichung von HRID 220519
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:20][C:21]1[C:25]([CH:26]=O)=[C:24]([CH3:28])[N:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:22]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:15][CH2:16][N:17]([CH2:26][C:25]4[C:21]([CH3:20])=[N:22][N:23]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:24]=4[CH3:28])[CH2:18][CH2:19]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 891791H-Pyrazole-4-carboxaldehyde, 3,5-dimethyl-1-phenyl-HCID 5049666Sodium triacetoxyborohydrideHCID 685942572-(4-Chlorophenyl)-3-(piperazin-1-yl)pyrazine

Produkt 1

HCID 685955403'-(4-Chlorophenyl)-4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine hydrochlorideAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Couple 3′-(4-chlorophenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.103 g, 0.400 mmol) and 3,5-dimethyl-1-phenyl 1H-pyrazole-4-carbaldehyde (0.083 g, 0.679 mmol) in the presence of acetic acid (0.035 mL, 0.61 mmol) and sodium triacetoxy-borohydride (0.105 g, 0.491 mmol) in DCE (5 mL) for 44 hr. Purify by silica gel chromatography, eluting with 0:100 to 10:90 methanol:DCM. Dissolve the free base in methanol and add ammonium chloride (6.0 mg, 0.2 mmol). Stir overnight, concentrate under reduced pressure, add diethyl ether and stir overnight. Isolate the solid product by filtration and vacuum dry overnight to give the title compound (0.0637 g, 46%). MS (ES): m/z=460 [M+H]+.

Aufarbeitung

  1. customPurify by silica gel chromatography
  2. washeluting with 0:100 to 10:90 methanol
  3. dissolutionDissolve the free base in methanol
  4. concentrationconcentrate under reduced pressure
  5. additionadd diethyl ether
  6. stirringstir overnight
  7. customIsolate the solid product
  8. filtrationby filtration and vacuum
  9. customdry overnight

Quellen und Nachweise

ORD-Eintrag
ord-19e2f948e9224b0982895768a13d3794
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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