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

HRID 1637692Notes

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-chloro-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester (prepared as described in Preparation E, 3.4343 g, 10.74 mmol) and 1-ethyl-propyl-amine (10 ml) in 10 ml of DMSO was heated at 120° C. for 15 hr. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give a yellow solid. The yellow solid was recrystallized with hexane to give 2.519 g (63%) of the title compound of Preparation F as white crystals, mp 106-107.5° C. Anal. for C22H30N2O3 (C,H,N). 1H NMR (CDCl3) δ 8.04(d,1H), 6.85(s,2H), 6.06(s,1H), 3.85(s,3H), 3.32(m,1H), 2.28(s,3H), 2.10(s,3H), 2.07(s,3H), 1.62(m,4H), 0.95(t,6H) ppm.

Workup

customThe mixture was quenched with water
extractionextracted with ethyl acetate
customThe organic layer was dried
concentrationconcentrated
customto give a yellow solid
customThe yellow solid was recrystallized with hexane
customto give

Sources & evidence

ORD record: ord-948f0daff0fa4d74bcb855eaab9ab4c0
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043260

Reaction notes

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