Thionyl Chloride → HCID 89443899, compound

HRID 526000Notes

Reaction equation

HRID 526000 reaction equation
S(Cl)(Cl)=O.[C:5]([C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[N:11][CH:12]=1)#[N:6]>C(O)CCC>[C:5]([C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:20])[CH2:15][CH2:16][C:17]([O:19][CH2:5][CH2:7][CH2:8][CH3:9])=[O:18])=[N:11][CH:12]=1)#[N:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 89449968HCID 89449968, compound

Product 1

HCID 89443899HCID 89443899, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of butan-1-ol (3 mL) was added dropwise thionyl chloride (2.73 mmol, 0.200 mL 3 eq). After 5 min, 4-[(5-cyano-2-pyridyl)amino]-4-oxo-butanoic acid A2 (prepared as described before, 200 mg, 0.912 mmol) was added to the solution. The reaction mixture was stirred overnight at room temperature. The reaction was stopped and the solution was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (2×). The combined organic layer was washed with a saturated solution of sodium hydrogenocarbonete and dried on magnesium sulfate, then concentrated under vacuum. The residue was first washed with cyclohexane and the solid obtained was purified by flash chromatography eluting with cyclohexane-ethyl acetate to give butyl 4-[(5-cyano-2-pyridyl)amino]-4-oxo-butanoate A66 (10%) and the by-product butyl 6-[(4-butoxy-4-oxo-butanoyl)amino]pyridine-3-carboxylate A67 (9%).

Workup

  1. customthe solution was partitioned between ethyl acetate and water
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic layer was washed with a saturated solution of sodium hydrogenocarbonete
  5. customdried on magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. washThe residue was first washed with cyclohexane
  8. customthe solid obtained
  9. customwas purified by flash chromatography
  10. washeluting with cyclohexane-ethyl acetate

Sources & evidence

ORD record
ord-9ef5ff19dd3540e4b99841310c518fc8
Source dataset
uspto-grants-2016_05
Patent number
US09345244B2

Reaction notes

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