4-Methylmorpholine → HCID 53484550, compound

HRID 716739Notes

Reaction equation

HRID 716739 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.Cl.[CH3:13][NH:14][O:15][CH3:16].CCN=C=NCCCN(C)C.Cl.CN1CCOCC1>CN(C=O)C.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([N:14]([O:15][CH3:16])[CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Product 1

HCID 53484550HCID 53484550, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (6-chloropyridin-3-yl)acetic acid (5.0 g), N,O-dimethylhydroxyamine hydrochloride (2.98 g), EDC.HCl (5.87 g), and N-methylmorpholine (9.6 mL) in DMF (70 mL) was stirred at room temperature for 4 days. Under ice cooling, water (150 mL) was added thereto, followed by extraction with EtOAc. The organic layer was sequentially washed with water and brine and was dried over Na2SO4. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (SNAP Cartridge HP-Sil: 50 g, mobile phase: n-hexane/EtOAc=75/25 to 0/100 (v/v)) to yield the title compound (3.56 g, light yellow oil).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was sequentially washed with water and brine
  3. dry with materialwas dried over Na2SO4
  4. customThe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (SNAP Cartridge HP-Sil: 50 g, mobile phase: n-hexane/EtOAc=75/25 to 0/100 (v/v))

Sources & evidence

ORD record
ord-9647f96b34cb47cdad81b00183a1ad9f
Source dataset
uspto-grants-2015_11
Patent number
US09193695B2

Reaction notes

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