Sodium Chloride → HCID 59673997, compound

HRID 1891054Notes

Reaction equation

HRID 1891054 reaction equation
[Br:1][C:2]1[C:3]([O:24][C@H:25]([CH3:29])[C@H](O)C)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:23])(=[N:17]C(OCC)=O)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:30]C[O-].[Na+].[Na+].[Cl-]>C(O)C>[Br:1][C:2]1[C:3]([O:24][CH2:25][CH3:29])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH2:23][CH3:30])(=[NH:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 2723922Sodium ethoxideHCID 59674023HCID 59674023, compound

Product 1

HCID 59673997HCID 59673997, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

28 mg (0.056 mmol) of (RS)—S-[4-({5-bromo-4-[(1R,2R)-2-hydroxy-1-methylpropoxy]pyrimidin-2-yl}amino)phenyl]-N-(ethoxycarbonyl)-S-methyl sulfoximide in 0.11 ml of ethanol is mixed with 0.32 ml (0.113 mmol) of a 0.35 molar solution of NaOEt in ethanol and stirred under reflux for 6 hours. The batch is stirred overnight at room temperature, and then added to a saturated NaCl solution. It is extracted with ethyl acetate, and the combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (DCM/EtOH 85:15). 9 mg (0.023 mmol, corresponding to 42% of theory) of the product is obtained.

Workup

  1. temperatureunder reflux for 6 hours
  2. stirringThe batch is stirred overnight at room temperature
  3. extractionIt is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe remaining residue is purified by chromatography (DCM/EtOH 85:15)
  8. custom9 mg (0.023 mmol, corresponding to 42% of theory) of the product is obtained

Sources & evidence

ORD record
ord-50bde5a9d5794090a830c716ae5fd439
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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