Acetic Acid → 3'-(4-Fluorophenyl)-4-[2-(3-isobutyl-5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-ethyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine hydrochloride

HRID 220505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220505
[CH2:1]([C:5]1[C:9]([CH2:10][CH:11]=O)=[C:8]([CH3:13])[N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:6]=1)[CH:2]([CH3:4])[CH3:3].[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[N:29][CH:30]=[CH:31][N:32]=2)=[CH:23][CH:22]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)[Cl:58]>>[ClH:58].[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([N:33]3[CH2:34][CH2:35][N:36]([CH2:11][CH2:10][C:9]4[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[N:6][N:7]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=5)[C:8]=4[CH3:13])[CH2:37][CH2:38]3)=[N:29][CH:30]=[CH:31][N:32]=2)=[CH:23][CH:22]=1

Komponenten

6

Edukt 5

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazineHCID 86641652(3-Isobutyl-5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-acetaldehyde

Produkt 1

HCID 685945743'-(4-Fluorophenyl)-4-[2-(3-isobutyl-5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-ethyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine hydrochlorideAusbeute 50 %

Versuchsvorschrift

Combine (3-isobutyl-5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-acetaldehyde (0.21 g, 0.82 mmol), 3′-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.21 g, 0.82 mmol) in DCM (10 mL) and stir at room temperature for 15 min. Add glacial acetic acid (0.07 mL, 1.23 mmol) then sodium triacetoxyborohydride (0.26 g, 1.23 mmol). Stir at room temperature for 20 hr. Concentrate, then purify using SCX chromatography and further purify using silica gel chromatography, eluting with 5% 7 M ammonia in methanol:DCM. Dissolve the free base in methanol (5 mL) and treat with ammonium chloride (0.022 g). Concentrate the resulting solution to give the title compound as a white powder (0.22 g, 50%). MS: m/z=500.3 [M+H]+.

Aufarbeitung

  1. concentrationConcentrate
  2. custompurify
  3. customfurther purify
  4. washeluting with 5% 7 M ammonia in methanol
  5. dissolutionDissolve the free base in methanol (5 mL)
  6. additiontreat with ammonium chloride (0.022 g)
  7. concentrationConcentrate the resulting solution

Quellen und Nachweise

ORD-Eintrag
ord-3118001bfa0546168184abf0e0c093a0
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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