Sodium ethoxide → HCID 71515605, compound

HRID 2277744Notes

Reaction equation

HRID 2277744 reaction equation
C([O-])C.[Na+].C(OC(=O)[N:9]=[S:10]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]2[N:26]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[O:34][CH3:35])[C:24]([F:36])=[CH:23][N:22]=2)[CH:15]=1)([CH3:12])=[O:11])C>CCO.[Cl-].[Na+]>[F:36][C:24]1[C:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[O:34][CH3:35])=[N:26][C:21]([NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([CH2:13][S:10]([CH3:12])(=[NH:9])=[O:11])[CH:15]=2)=[N:22][CH:23]=1

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 71515604HCID 71515604, compound

Product 1

HCID 71515605HCID 71515605, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 5234Sodium ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

A freshly prepared 1.5M solution of sodium ethanolate in EtOH (0.37 mL; 0.56 mmol) was added under argon to a solution of (rac)-ethyl[(3-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]-amino}benzyl)(methyl)oxido-λ6-sulfanylidene]carbamate (53 mg; 0.11 mmol) in EtOH (1.0 mL). The batch was stirred at 60° C. for 5 hours. After cooling the batch was diluted with saturated aqueous sodium chloride solution and extracted with ethyl acetate (3×). The combined organic phases were filtered using a Whatman filter and concentrated. The residue was purified by chromatography (DCM/EtOH 95:5) to give the desired product (33 mg; 0.08 mmol).

Workup

  1. temperatureAfter cooling the batch
  2. extractionextracted with ethyl acetate (3×)
  3. filtrationThe combined organic phases were filtered
  4. filtrationfilter
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (DCM/EtOH 95:5)

Sources & evidence

ORD record
ord-1487160af2da46fba0a456bfb543526b
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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