Potassium Carbonate → N-(3-Methoxycarbonylphenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

HRID 392427Notes

Reaction equation

HRID 392427 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([NH:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[CH2:19]([S:21](Cl)(=[O:23])=[O:22])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>ClC(Cl)C.N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([N:11]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[S:21]([CH2:19][CH3:20])(=[O:23])=[O:22])[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11667Ethanesulfonyl chlorideHCID 43139315Methyl 3-((pyridin-3-ylmethyl)amino)benzoate

Product 1

HCID 23521670N-(3-Methoxycarbonylphenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamineYield 49%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Into a 0° C. solution of N-(3-methoxycarbonylphenyl) pyrid-3-ylmethylamine (204 g, 0.842 mole, 1 eq) in dichloroethane (3610 mL) and pyridine (1775 mL) was added ethanesulfonyl chloride (114 mL, 1.2 mole, 1.43 eq). The reaction was allowed to warm to room temperature overnight. The dark red reaction was stirred with potassium carbonate (204 g) for 30 minutes and then filtered and concentrated to dryness. The residue was purified by Biotage, eluting with 3:1 to 2:1 DCM/EtOAc mixture to give the title compound as a white solid (137.0 g, 49% yield).

Workup

  1. customThe dark red reaction
  2. filtrationfiltered
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by Biotage
  5. washeluting with 3:1 to 2:1 DCM/EtOAc mixture

Sources & evidence

ORD record
ord-32fc6db824284f9f91ed2dd5ed977606
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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