3-Pentanamine → HCID 24806452, compound

HRID 967982Notes

Reaction equation

HRID 967982 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]([Br:20])=[CH:15][C:14]=1[CH3:21].[CH2:23]([CH:25]([NH2:28])[CH2:26][CH3:27])[CH3:24]>CS(C)=O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([NH:28][CH:25]([CH2:26][CH3:27])[CH2:23][CH3:24])=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([Br:20])=[CH:15][C:14]=1[CH3:21]

Participants

4

Reactant 2

HCID 120193-PentanamineHCID 24806457HCID 24806457, compound

Product 1

HCID 24806452HCID 24806452, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-chloro-6-methyl-2-(4-bromo-2,6-dimethyl-phenoxy)-nicotinic acid methyl ester and 1-ethyl-propyl-amine in DMSO was heated at 120° C. for 16 hr. 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 using hexane to 3% ethyl acetate in hexane as eluent to give to the title compound as a white solid. 1H NMR(CDCl3) d 8.1(d, 1H), 7.18(s, 2H), 6.08(s, 1H), 3.87(s, 3H), 3.35(m, 1H), 2.10(s, 3H), 2.08(s, 6H), 1.4-1.7(m, 4H), 0.96(t, 6H) ppm.

Workup

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

Sources & evidence

ORD record
ord-40b52eb7fe654069914b482c11eaa06d
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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