Sodium Methoxide → HCID 86667440, compound

HRID 527039Notes

Reaction equation

HRID 527039 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][P:25]([O:29][CH3:30])([O:27][CH3:28])=[O:26])[CH2:19]4)[C:14]([F:31])=[CH:13][N:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][P:25](=[O:26])([O:29][CH3:30])[O:27][CH3:28])[CH2:19]4)[C:14]([F:31])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86667441HCID 86667441, compound2×

Product 1

HCID 86667440HCID 86667440, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-N-[(3S)-1-(dimethoxyphosphorylmethyl)-3-piperidyl]-5-fluoro-pyrimidin-4-amine, 56a, (1.00 g, 1.61 mmol) in MeOH (40 mL) was added sodium methanolate (20 mL of 25% w/v, 92.55 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. All volatiles were removed at reduced pressure and the resulting residue was diluted with aqueous saturated NH4Cl solution and extracted twice with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified via silica gel chromatography using 0-10% MeOH:CH2Cl2 gradient to provide 270 mg of a white solid.

Workup

  1. customAll volatiles were removed at reduced pressure
  2. additionthe resulting residue was diluted with aqueous saturated NH4Cl solution
  3. extractionextracted twice with CH2Cl2
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-f65949e3d5bf461bb6d6a85ecdd211b2
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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