1,2-Dichloroethane → HCID 68595295, compound

HRID 220511Notes

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.[OH:20][CH2:21][CH2:22][CH2:23][N:24]1[CH:28]=[C:27]([CH:29]=O)[CH:26]=[N:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:45]CCCl>>[ClH:45].[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]([CH2:29][C:27]4[CH:26]=[N:25][N:24]([CH2:23][CH2:22][CH2:21][OH:20])[CH:28]=4)[CH2:18][CH2:19]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 5049666Sodium triacetoxyborohydride

HCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazine

HCID 87510032HCID 87510032, compound

Product 1

HCID 68595295HCID 68595295, compoundYield 45%

Procedure

Dissolve 3′-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.150 g, 0.581 mmol) in DCE (5 mL). Add 1-(3-hydroxy-propyl)-1H-pyrazole-4-carbaldehyde (0.107 g, 0.697 mmol) followed by sodium triacetoxyborohydride (0.185 g, 0.872 mmol) and stir at room temperature for 18 hr. Purify via SCX chromatography, followed by silica gel chromatography (0:100 hexanes:ethyl acetate then 10:90 methanol:ethyl acetate), followed by reverse phase chromatography, SCX chromatography and silica gel chromatography (100:0 to 0:100 hexanes:ethyl acetate then 10:90 methanol:ethyl acetate to 20:80 methanol:ethyl acetate), to give the free base of the title compound (103 mg, 45%). Dissolve the free base (0.099 g, 0.251 mmol) in methanol and add a solution of ammonium chloride (0.013 g, 0.251 mmol) in a minimal volume of methanol. Shake for 18 hr. at ambient temperature and concentrate to give the title compound (105 mg, 97%). MS (ES): m/z=397 [M+H]+.

Workup

customPurify via SCX chromatography

Sources & evidence

ORD record: ord-35ad6b221dec4f8b858efd0f61cac422
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202873B2

Reaction notes

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