Triethylamine → 3-(4-{[3-(4-Tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)-1-cyclopentyl-1-methylurea

HRID 546592Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=O)[O:28]CC)[CH:21]=3)[C:12]2=[O:32])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:33][NH:34][CH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.C(N(CC)CC)C>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=[O:28])[N:34]([CH:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[CH3:33])[CH:21]=3)[C:12]2=[O:32])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 0.16 g of ethyl (4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)-carbamate obtained in stage a) below in 2 mL of tetrahydrofuran are added successively 0.368 mL of N-methylcyclopentylamine and 0.512 mL of triethylamine. The reaction mixture is heated by microwave at 130° C. for 3 hours and then concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of ethyl acetate and cyclohexane (60/40 by volume) to give 0.048 g of 3-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)-1-cyclopentyl-1-methylurea, the characteristics of which are as follows:

Workup

concentrationconcentrated under reduced pressure
customThe residue is purified by chromatography on a column of silica
washeluting with a mixture of ethyl acetate and cyclohexane (60/40 by volume)

Sources & evidence

ORD record: ord-962c1dfb6a284a349eda42c8816ac2b2
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935819B2

Reaction notes

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