1H-Pyrazole-4-carboxaldehyde, 3,5-dimethyl-1-phenyl- → 3'-(3,4-Dichloro-phenyl)-4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl hydrochloride

HRID 220503Notes

Reaction equation

HRID 220503 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[N:11][CH:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:21][C:22]1[C:26]([CH:27]=O)=[C:25]([CH3:29])[N:24]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([N:15]3[CH2:16][CH2:17][N:18]([CH2:27][C:26]4[C:22]([CH3:21])=[N:23][N:24]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:25]=4[CH3:29])[CH2:19][CH2:20]3)=[N:11][CH:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 891791H-Pyrazole-4-carboxaldehyde, 3,5-dimethyl-1-phenyl-HCID 5049666Sodium triacetoxyborohydrideHCID 685943053'-(3,4-dichloro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

Product 1

HCID 685961173'-(3,4-Dichloro-phenyl)-4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl hydrochlorideYield 33.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Combine 3′-(3,4-dichloro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.0590 g, 0.191 mmol) and 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde (0.0592 gm, 0.300 mmol) in DCE (5 mL), stir 10 min, and add sodium triacetoxyborohydride (0.838 gm, 0.400 mmol). Stir at ambient temperature for 44 hr. and purify by SCX chromatography, followed by silica gel chromatography, eluting with 0-50% THF in hexanes to give the free base of the title compound (0.017 gm, 18%). Convert the free base to the hydrochloride salt by addition of 0.17 mL of a 0.2 M solution of ammonium chloride in methanol to give the title compound (0.017 gm). MS (ES+) m/z: 494 [M+H]+.

Workup

  1. customand purify by SCX chromatography
  2. washeluting with 0-50% THF in hexanes

Sources & evidence

ORD record
ord-1638c9380f334d96a17b6826c6f41a77
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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