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1,2-Dichloroethane → 4-(1-Ethyl-5-methyl-1h-pyrazol-4-ylmethyl)-3'-phenyl-3,4,5,6-tetrahydro-2h-[1,2']bipyrazine hydrochloride

HRID 220500
Notes
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Reaction equation

HRID 220500 reaction equation
[C:1]1([C:7]2[C:8]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([N:21]1[C:25]([CH3:26])=[C:24]([CH:27]=O)[CH:23]=[N:22]1)[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl:47]CCCl>>[ClH:47].[CH2:19]([N:21]1[C:25]([CH3:26])=[C:24]([CH2:27][N:16]2[CH2:17][CH2:18][N:13]([C:8]3[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:12][CH:11]=[CH:10][N:9]=3)[CH2:14][CH2:15]2)[CH:23]=[N:22]1)[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 5732041-Ethyl-5-methyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 595112832-Phenyl-3-(piperazin-1-yl)pyrazine

Product 1

HCID 68594944
4-(1-Ethyl-5-methyl-1h-pyrazol-4-ylmethyl)-3'-phenyl-3,4,5,6-tetrahydro-2h-[1,2']bipyrazine hydrochloride
Yield 52%

Procedure

Dissolve 3′-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.28 g, 1.18 mmol) in DCE (5 mL). Add 1-ethyl-5-methyl-1H-pyrazole-4-carbaldehyde (0.24 g, 1.76 mmol) and stir at room temperature for 20 min. Add sodium triacetoxyborohydride (0.5 g, 2.36 mmol) followed by acetic acid (0.07 mL, 1.24 mmol). Stir at room temperature for 16 hr. Purify via SCX chromatography, followed by silica gel chromatography, eluting with 3:97 to 7:93 7 N ammonia in methanol:ethyl acetate, to give the free base of the title compound (0.22 g, 52%). MS (ES): m/z=363.3 [M+H]+.

Workup

  1. customPurify via SCX chromatography
  2. washeluting with 3:97 to 7:93 7 N ammonia in methanol

Sources & evidence

ORD record
ord-0eec44e2033a4e72a02b88ed4d1402c0
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202873B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes