1,2-Dichloroethane → HCID 68594581, compound

HRID 220513Notes

Reaction equation

HRID 220513 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][CH:21]([CH3:30])[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: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]([CH2:28][C:26]4[CH:25]=[N:24][N:23]([CH2:22][CH:21]([OH:20])[CH3:30])[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 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazineHCID 875099441-(2-hydroxypropyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 68594581HCID 68594581, compound

Procedure

Dissolve 3′-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.160 g, 0.619 mmol) in DCE (5 mL). Add racemic 1-(2-hydroxy-propyl)-1H-pyrazole-4-carbaldehyde (0.175 g, 1.14 mmol) followed by sodium triacetoxyborohydride (0.262 g, 1.24 mmol) and stir at room temperature for 72 hr. Purify via SCX chromatography, followed by silica gel chromatography, eluting with 100:0 to 0:100 hexanes:ethyl acetate then 10:90 methanol:ethyl acetate, to give the racemic mixture of the free bases of the title compounds (223 mg, 91%).

Workup

  1. customPurify via SCX chromatography
  2. washeluting with 100:0 to 0:100 hexanes
  3. customethyl acetate then 10:90 methanol:ethyl acetate, to give

Sources & evidence

ORD record
ord-6916dcc017e842b4bdb1e76a1c02f1df
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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