1,2-Dichloroethane → 3'-(4-Fluoro-phenyl)-4-[1-(1-methyl-1h-imidazol-4-yl)-1h-pyrazol-4-ylmethyl]-3,4,5,6-tetrahydro-2h-[1,2']bipyrazinyl hydrochloride

HRID 220512Notes

Reaction equation

HRID 220512 reaction equation
[F: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][N:21]1[CH:25]=[C:24]([N:26]2[CH:30]=[C:29]([CH:31]=O)[CH:28]=[N:27]2)[N:23]=[CH:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl:51]CCCl>>[ClH:51].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:15][CH2:16][N:17]([CH2:31][C:29]4[CH:28]=[N:27][N:26]([C:24]5[N:23]=[CH:22][N:21]([CH3:20])[CH:25]=5)[CH:30]=4)[CH2:18][CH2:19]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazineHCID 866416551-(1-Methyl-1H-imidazol-4-yl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 685957203'-(4-Fluoro-phenyl)-4-[1-(1-methyl-1h-imidazol-4-yl)-1h-pyrazol-4-ylmethyl]-3,4,5,6-tetrahydro-2h-[1,2']bipyrazinyl hydrochlorideYield 71%

Procedure

Dissolve 3′-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.053 g, 0.204 mmol) in DCE (2.1 mL). Add 1-(1-methyl-1H-imidazol-4-yl)-1H-pyrazole-4-carbaldehyde (0.036 g, 0.204 mmol) and stir at ambient temperature for 1 hr. Add sodium triacetoxyborohydride (0.065 g, 0.306 mmol) and acetic acid (19 μL) and stir at room temperature for 72 hr. Purify via SCX chromatography, followed by silica gel chromatography (50:50 to 0:100 hexanes:ethyl acetate then 10:90 to 20:80 methanol:ethyl acetate) to give the free base of the title compound (61 mg, 71%).

Workup

  1. customPurify via SCX chromatography

Sources & evidence

ORD record
ord-346fcacab74048efbbfef9e7f94a731a
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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