HCID 86605365, compound → HCID 86605366, compound

HRID 2195076Notes

Reaction equation

HRID 2195076 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Cl:39])[C:8]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[N:21]=[C:20]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][C@H:32]4[CH3:37])[N:19]=3)[CH:14]([CH3:38])[CH2:13]2)=[N:9][C:10]=1Br)=[O:4].[H][H]>C1COCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Cl:39])[C:8]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[C:22]([C:24]4[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=4)[N:21]=[C:20]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH:32]4[CH3:37])[N:19]=3)[C@H:14]([CH3:38])[CH2:13]2)=[N:9][CH:10]=1)=[O:4]

Participants

5

Reactant 2

HCID 86605365HCID 86605365, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86605366HCID 86605366, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Stir a solution of 6′-bromo-3′-chloro-4-[6-(4-fluoro-phenyl)-2-(3-(R)-methyl-morpholin-4-yl)-pyrimidin-4-yl]-3-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-carboxylic acid methyl ester (3 g) in 100 mL of THF with 5% palladium on carbon (300 mg) under 1 atmosphere of hydrogen gas for several days. Filter the mixture through celite and concentrate under reduced pressure. Partition the residue between saturated NaHCO3 solution and EtOAc. Dry (Na2SO4) the organic layer and concentrate under reduced pressure. Purify using flash column chromatography eluting with a gradient EtOAc/hexanes solvent system to give the title compound.

Workup

  1. filtrationFilter the mixture through celite
  2. concentrationconcentrate under reduced pressure
  3. customPartition the residue between saturated NaHCO3 solution and EtOAc
  4. dry with materialDry (Na2SO4) the organic layer
  5. concentrationconcentrate under reduced pressure
  6. customPurify
  7. washeluting with a gradient EtOAc/hexanes solvent system

Sources & evidence

ORD record
ord-0ebec8bd8cea48049ce38f1351c89102
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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