Sodium Methoxide → HCID 68007798, compound

HRID 527006Notes

Reaction equation

HRID 527006 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][C@@:20]([CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])([OH:24])[CH2:19]4)[C:14]([F:30])=[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][C@@:20]([CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])([OH:24])[CH2:19]4)[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68007791HCID 68007791, compound2×

Product 1

HCID 68007798HCID 68007798, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1R,3S)-3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-(methylsulfonylmethyl)cyclohexanol, 49f, (0.045 g, 0.074 mmol) in MeOH (2 mL) was added NaOMe (2 mL of 25% w/v, 9.255 mmol). The reaction mixture was allowed to stir at room temperature for 5 minutes, after which the mixture was quenched with the addition of aqueous saturated NH4Cl solution and then diluted with EtOAc. The layers were separated and the organic was washed with brine, dried over MgSO4, filtered and evaporated to dryness. The crude residue was purified via silica gel chromatography (0-10% MeOH/CH2Cl2 gradient).

Workup

  1. customafter which the mixture was quenched with the addition of aqueous saturated NH4Cl solution
  2. additiondiluted with EtOAc
  3. customThe layers were separated
  4. washthe organic was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude residue was purified via silica gel chromatography (0-10% MeOH/CH2Cl2 gradient)

Sources & evidence

ORD record
ord-310d1a3bbf724e949b408d30342add15
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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