Sodium Methoxide → HCID 71251333, compound

HRID 2171855Notes

Reaction equation

HRID 2171855 reaction equation
[CH:1]1([CH:5]([NH:11][C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([F:28])[CH:26]=4)[N:21](S(C4C=CC(C)=CC=4)(=O)=O)[CH:20]=3)[N:13]=2)[CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH2:3][CH2:2]1.C1(C(NC2C(F)=CN=C(C3C4C(=NC=C(F)C=4)N(S(C4C=CC(C)=CC=4)(=O)=O)C=3)N=2)CC([O-])=O)CCC1.C[O-].[Na+]>CO>[CH:1]1([CH:5]([NH:11][C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([F:28])[CH:26]=4)[NH:21][CH:20]=3)[N:13]=2)[CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 71251332HCID 71251332, compoundHCID 86714744HCID 86714744, compound

Product 1

HCID 71251333HCID 71251333, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a racemic solution of methyl 3-cyclobutyl-3-((5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)propanoate, 51a, (0.151 g, 0.280 mmol) in methanol (1.5 mL) was added NaOMe (1.5 mL of 25% w/v solution, 6.941 mmol). After stirring the reaction mixture at room temperature for 5 minutes, the mixture was quenched with aqueous saturated NH4Cl solution and diluted with EtOAc and water. The layers were separated and the organic phase was washed with brine, dried (MgSO4), filtered and evaporated to dryness. The resulting crude residue was dissolved in a minimum volume of dichloromethane and purified via silica gel chromatography (0-100% EtOAc/Hexanes gradient) to afford 108 mg of the desired product: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=2.29 minutes (M+H) 388.07.

Workup

  1. customthe mixture was quenched with aqueous saturated NH4Cl solution
  2. additiondiluted with EtOAc and water
  3. customThe layers were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. dissolutionThe resulting crude residue was dissolved in a minimum volume of dichloromethane
  9. custompurified via silica gel chromatography (0-100% EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-359bbf26adaf401bbe5dea8636038e97
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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