Sodium hydride → HCID 58978002, compound

HRID 1179302Notes

Reaction equation

HRID 1179302 reaction equation
[CH3:1][N:2]([CH3:19])[S:3]([CH2:6][CH2:7][NH:8][C:9]1[C:10]([C:15]([O:17]C)=O)=[N:11][CH:12]=[CH:13][CH:14]=1)(=[O:5])=[O:4].[H-].[Na+].Cl[C:23](=[O:29])[CH2:24][C:25]([O:27][CH3:28])=[O:26]>C1COCC1.CO>[CH3:19][N:2]([CH3:1])[S:3]([CH2:6][CH2:7][N:8]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[C:15]([OH:17])=[C:24]([C:25]([O:27][CH3:28])=[O:26])[C:23]1=[O:29])(=[O:4])=[O:5]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 123460Methyl malonyl chlorideHCID 58977998HCID 58977998, compound

Product 1

HCID 58978002HCID 58978002, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-({2-[(dimethylamino)sulfonyl]ethyl}amino)pyridine-2-carboxylate (0.877 g, 3.05 mmol) was dissolved in dry THF (10 mL) and cooled to 0° C. NaH (338 mg, 60% suspension in oil, 8.45 mmol) was added and a precipitate formed. The slurry was treated with methyl 3-chloro-3-oxopropionate (0.410 mL, 3.82 mmol) and 3 drops of MeOH and allowed to warm and stir overnight. The reaction was concentrated somewhat in vacuo, then poured into water. The mixture was extracted once with CHCL3, then acidified and extracted repeatedly with CHCl3 until only a trace of UV active material is removed. The acidic organic extracts were dried over Na2SO4, filtered and evaporated to give the product as a pink foam.

Workup

  1. customa precipitate formed
  2. temperatureto warm
  3. concentrationThe reaction was concentrated somewhat in vacuo
  4. additionpoured into water
  5. extractionThe mixture was extracted once with CHCL3
  6. extractionextracted repeatedly with CHCl3 until only a trace of UV active material
  7. customis removed
  8. dry with materialThe acidic organic extracts were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-4ecfbc9ac6024c2eb2c5894241376ae4
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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