Sodium Hydroxide → 3'-(4-Methanesulfonylphenyl)-4-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

HRID 220522Notes

Reaction equation

HRID 220522 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:13][CH:14]=[CH:15][N:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:23][N:24]1[C:28]([CH3:29])=[C:27]([CH:30]=O)[C:26]([CH3:32])=[N:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[OH-].[Na+]>O1CCCC1>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([N:17]3[CH2:22][CH2:21][N:20]([CH2:30][C:27]4[C:26]([CH3:32])=[N:25][N:24]([CH3:23])[C:28]=4[CH3:29])[CH2:19][CH2:18]3)=[N:13][CH:14]=[CH:15][N:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 7365151,3,5-trimethyl-1H-pyrazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 685945073'-(4-methanesulfonylphenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

Product 1

HCID 593220653'-(4-Methanesulfonylphenyl)-4-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazineYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Suspend 3′-(4-methanesulfonylphenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.191 g, 0.60 mmol) in tetrahydrofuran (4 mL). Add 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (0.087 g, 0.63 mmol) in tetrahydrofuran (435 μL), then sodium triacetoxyborohydride (0.13 g, 0.63 mmol). Subject reaction to ultrasound for 30 sec. then stir under nitrogen at room temperature for 7 hr. Add saturated aqueous sodium hydrogen carbonate (10 mL) followed by 2 N sodium hydroxide (1 mL) to the mixture and extract with DCM (3×20 mL). Pass the combined DCM extracts through an IST Phase Separator Frit®, concentrate and purify (silica gel chromatography, eluting with 0:100 to 12:88 methanol:DCM), to give the title compound (241.9 mg, 91%). MS (ES): m/z=441.2 [M+H]+.

Workup

  1. customreaction
  2. extractionextract with DCM (3×20 mL)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 0:100 to 12:88 methanol:DCM)

Sources & evidence

ORD record
ord-1de79b232b7c47c58f019b8f0d2f47a9
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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