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

HRID 967989Notes

Reaction equation

HRID 967989 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-f2fd09205608405a98cfdec4ff18b02e
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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