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

HRID 1245761Notes

Reaction equation

HRID 1245761 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 concentratd 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. customto give 1.796 g of crude material
  7. customThe crude material was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-e2257505e6c04b879d2ee4c153701f14
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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