2-(Dimethylamino)ethanol → 5-(2-(dimethylamino)-ethoxy)-N-methoxy-N-methylpicolinamide

HRID 626151Notes

Reaction equation

HRID 626151 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])=[N:6][CH:7]=1.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 866889815-hydroxy-N-methoxy-N-methylpicolinamide

Product 1

HCID 896576755-(2-(dimethylamino)-ethoxy)-N-methoxy-N-methylpicolinamideYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-hydroxy-N-methoxy-N-methylpicolinamide (1.0 eq), 2-(dimethylamino)ethanol (1.2 eq) and PPh3 (1.2 eq) in 5 mL anhydrous THF under nitrogen was added DIAD (1.2 eq) dropwise at 0° C. The reaction was stirred overnight at rt., quenched with water, and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography to give the desired product (40% yield).

Workup

  1. custom, quenched with water
  2. extractionextracted with EtOAc
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-dc277a7a034a44149062d0704dd6defd
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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