3-Pentanamine → 4-[Ethyl-(2-hydroxy-ethyl)-amino]-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester

HRID 2307961Notes

Reaction equation

HRID 2307961 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9](Cl)=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21].C([CH:25]([NH2:28])[CH2:26]C)C.CN1CC[CH2:32][C:31]1=[O:35]>>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([N:28]([CH2:25][CH3:26])[CH2:32][CH2:31][OH:35])=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21]

Participants

4

Reactant 3

HCID 120193-PentanamineHCID 13387N-methyl-2-pyrrolidoneHCID 248056514-Chloro-2-(2,4,6-trimethyl-phenoxy)-6-methyl-nicotinic acid methyl ester

Product 1

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

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloro-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester and 1-ethyl-propyl-amine in 1-methyl-2-pyrrolidinone was heated at 130° C. until starting material was consumed. The mixture was quenched with water, brine and extracted with ethyl acetate. 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 6.85(s,2H), 6.40(s,1H), 3.88(s,3H), 3.73(t,2H), 3.43(t,2H), 3.31(q,2H), 2.27(s,3H), 2.22(s,3H), 2.06(s,6H), 1.15(t,3H) ppm.

Workup

  1. customwas consumed
  2. customThe mixture was quenched with water, brine
  3. extractionextracted with ethyl acetate
  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-e617806b7ed040888f0e18e5a2e45e0d
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

Loading…