1,2-Dichloroethane → HCID 68595010, compound

HRID 220507Notes

Reaction equation

HRID 220507 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][N:23]1[CH:27]=[C:26]([CH:28]=O)[CH:25]=[N:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:44]CCCl>>[ClH:44].[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]([CH2:28][C:26]4[CH:25]=[N:24][N:23]([CH2:22][CH2:21][OH:20])[CH:27]=4)[CH2:18][CH2:19]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 247026081-(2-hydroxyethyl)-1H-pyrazole-4-carbaldehydeHCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazine

Product 1

HCID 68595010HCID 68595010, compoundYield 62%

Procedure

Dissolve 3′-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.320 g, 1.24 mmol) in DCE (5 mL). Add 1-(2-hydroxy-ethyl)-1H-pyrazole-4-carbaldehyde (0.243 g, 1.73 mmol), and stir at room temperature. Add sodium triacetoxyborohydride (0.394 g, 1.86 mmol) and stir at room temperature for 18 hr. Purify via SCX chromatography, followed by silica gel chromatography, eluting with 20:80 then 0:100 hexanes:ethyl acetate then 5:95 methanol:ethyl acetate then 10:90 methanol:ethyl acetate, to give the free base of the title compound (296 mg, 62%). Dissolve the free base (0.290 g, 0.760 mmol) in acetonitrile and add 1N aqueous HCl solution (913 μL, 0.913 mmol) and shake at ambient temperature for 30 min. Freeze and lyophilize to give the title compound (315 mg, 99%). MS (ES): m/z=383 [M+H]+.

Workup

  1. customPurify via SCX chromatography
  2. washeluting with 20:80

Sources & evidence

ORD record
ord-a4ea4eaacb9c452998c1557e13a5150f
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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