Triethylamine → 4-[Ethyl-(2-methanesulfonyloxy-ethyl)-amino]-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester

HRID 1831665Notes

Reaction equation

HRID 1831665 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[C:9]([N:10]([CH2:14][CH3:15])[CH2:11][CH2:12][OH:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[O:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26].[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[C:4]1[C:9]([N:10]([CH2:14][CH3:15])[CH2:11][CH2:12][O:13][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[O:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 695875454-[Ethyl-(2-hydroxy-ethyl)-amino]-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester

Product 1

HCID 865964814-[Ethyl-(2-methanesulfonyloxy-ethyl)-amino]-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[ethyl-(2-hydroxy-ethyl)-amino]-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester, methanesulfonyl chloride and triethylamine in methylene chloride was stirred at rt until all starting material were consumed. The mixture was quenched with water, brine and extracted with methylene chloride. The organic layer was dried and concentrated to dryness. The residue was purified through silica gel column chromatography to give the title compound. 1H NMR(CDCl3) d 6.83(s,2H), 6.25(s,1H), 4.34(t,2H), 3.86(s,3H), 3.6(t,2H), 3.38(t,2H), 3.09s,3H), 2.25(s,3H), 2.20(s,3H), 2.04(s,6H), 1.18(t,3H) ppm.

Workup

  1. customwere consumed
  2. customThe mixture was quenched with water, brine
  3. extractionextracted with methylene chloride
  4. customThe organic layer was dried
  5. concentrationconcentrated to dryness
  6. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-5b2b3102fced4940a29b968f6951dd8f
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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