3-Pentanamine → 2-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester

HRID 1760702Notes

Reaction equation

HRID 1760702 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9](Cl)=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[Cl:12].[CH2:14]([CH:16]([NH2:19])[CH2:17][CH3:18])[CH3:15]>CS(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([NH:19][CH:16]([CH2:17][CH3:18])[CH2:14][CH3:15])=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[Cl:12]

Participants

4

Reactant 2

HCID 120193-PentanamineHCID 15171394Methyl 2,4-dichloro-6-methylnicotinate

Product 1

HCID 248068762-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2,4-dichloro-6-methyl-nicotinic acid methyl ester (2.228 g, 10.13 mmol) and 1-ethyl-propyl amine (1.762 g, 20.26 mmol) in DMSO (4 ml) was heated at 110° C. for 5 hours, then at room temperature overnight. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 1.796 g of crude material. The crude material was purified through silica gel column chromatography using chloroform to 5% methanol in chloroform as eluent to give 1.167 g (43%) of the title compound as a colorless oil. 1H NMR (CDCl3) δ 7.14 (brs, 1H), 6.27 (s, 1H), 3.86 (s, 3H), 3.27 (m, 1H), 2.33 (s, 3H), 1.3-1.6 (m, 4H), 0.88 (t, 6H) ppm.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customto give 1.796 g of crude material
  8. customThe crude material was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-9dab899d372a4a419e08fff779ed4359
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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