3-Pentanamine → 4-(1-Ethyl-prop-2-ynylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester

HRID 967983Notes

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].[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])[C:23]#[CH: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]([CH3:20])=[CH:15][C:14]=1[CH3:21]

Participants

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 DMSO was heated at 130° C. overnight. 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 8.26(d, 1H), 6.87(s, 2H), 6.26(s, 1H), 4.11(m, 1H), 3.87(s, 3H), 2.324(m, 1H), 2.30(s, 3H), 2.17s, 3H), 2.08(s, 6H), 1.92(q, 2H), 1.16(t, 3H) ppm.

Workup

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

Sources & evidence

ORD record: ord-453adb77b7934f3c9db2dc24d474bb25
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956047B1

Reaction notes

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