1,2-Dichloroethane → HCID 68594778, compound

HRID 220514Notes

Reaction equation

HRID 220514 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.[F:20][C:21]([F:33])([F:32])[CH:22]([OH:31])[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:48]CCCl>>[ClH:48].[F:33][C:21]([F:20])([F:32])[CH:22]([OH:31])[CH2:23][N:24]1[CH:28]=[C:27]([CH2:29][N:17]2[CH2:16][CH2:15][N:14]([C:9]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[N:13][CH:12]=[CH:11][N:10]=3)[CH2:19][CH2:18]2)[CH:26]=[N:25]1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazineHCID 87510074HCID 87510074, compound

Product 1

HCID 68594778HCID 68594778, compound

Procedure

Dissolve 3′-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.143 g, 0.554 mmol) in DCE (5 mL). Add racemic 1-(3,3,3-trifluoro-2-hydroxy-propyl)-1H-pyrazole-4-carbaldehyde (0.236 g, 1.13 mmol) followed by sodium triacetoxyborohydride (0.235 g, 1.11 mmol) and stir at room temperature for 18 hr. Purify via SCX chromatography, followed by silica gel chromatography (eluting with 100:0 to 0:100 hexanes:ethyl acetate then 3:97 methanol:ethyl acetate), to give a racemic mixture of the free bases of the racemic title compounds (166 mg, 67%).

Workup

  1. customPurify via SCX chromatography
  2. washeluting with 100:0 to 0:100 hexanes
  3. customethyl acetate then 3:97 methanol:ethyl acetate), to give

Sources & evidence

ORD record
ord-012b92ad11394b34bd19eb57e4c07826
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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