Cyclohexaneacetic acid, 4-[4-[6-(aMinocarbonyl)-3,5-diMethyl-2-pyrazinyl]phenyl]-, Methyl ester, trans- synthesis

5synthesis methods

Product Name:Cyclohexaneacetic acid, 4-[4-[6-(aMinocarbonyl)-3,5-diMethyl-2-pyrazinyl]phenyl]-, Methyl ester, trans-
CAS Number:1166831-68-0
Molecular formula:C22H27N3O3
Molecular Weight:381.47

1166828-19-8 Synthesis

6-Chloro-3,5-diMethylpyrazine-2-carboxaMide

1166828-19-8
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701232-69-1 Synthesis

2-[(1r,4r)-4-[4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclohexyl]acetate

701232-69-1
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Cyclohexaneacetic acid, 4-[4-[6-(aMinocarbonyl)-3,5-diMethyl-2-pyrazinyl]phenyl]-, Methyl ester, trans-

1166831-68-0
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Yield:1166831-68-0 100%

Reaction Conditions:

with potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,2-dimethoxyethane;ethanol;water at 80; for 16 h;

Steps:

1.8

Intermediate 1-8: methyl 2-(( ls,4s)-4-(4-(6-carbamoyl-3.,5-dimethylpyrazin-2- vDphenvDcyclohexyDacetateA solution of 6-chloro-3,5-dimethylpyrazine-2-carboxamide (see Intermediate 21-4) (3.15 g, 16.97 mmol), methyl 2-((ls,4s)-4-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)cyclohexyl)acetate (see Intermediate 64-8) (6.08 g, 16.97 mmol) and tripotassium phosphate (4.32 g, 20.37 mmol) in DME (120 mL), ethanol (75 mL) and water (30.0 mL) were degassed before addition of (l,l'-bis(diphenylphosphino)ferrocene)- dichloropalladium(II) (0.698 g, 0.85 mmol). The reaction mixture was heated to 80 ⁰C, under nitrogen, and left to stir overnight for 16 hrs. The reaction mixture was allowed to cool to room temperature and then evaporated. The crude product was partitioned between water (250 mL) and EtOAc (250 mL). The catalyst was filtered off from the biphasic mixture. The organic phase was separated and washed with brine (100 mL), dried (Na₂SO₄) and evaporated. The crude product was purified by flash silica chromatography, elution gradient 5 to 90% EtOAc in isohexane on 330g silicyle column. Pure fractions were evaporated to dryness to afford the title compound (6.47 g, 100 %) as a yellow solid.[ ¹H NMR (400.132 MHz, DMSO) δ 1.10 - 1.21 (2H, m), 1.46 - 1.56 (2H, m), 1.73 - 1.86 (5H, m), 2.25 (2H, d), 2.58 (3H, s ), 2.73 (3H, s), 3.28 (IH, s), 3.60 (3H, s), 7.35 (2H, d), 7.58 (IH, s), 7.64 (2H, d), 7.97 (IH, s); HPLC tR= 2.53 min.]

References:

WO2009/81195,2009,A1 Location in patent:Page/Page column 169

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1166827-49-1 Synthesis

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References