Tetrahydrofuran → Methyl 5-formyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate
Reaction equation
C([N:9]1[C:13](=[O:14])[C:12]([CH:16]([CH3:18])[CH3:17])([CH3:15])[N:11]=[C:10]1[C:19]1[N:28]=[CH:27][C:26](C(Br)Br)=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])(=O)C1C=CC=CC=1.C(NCCN)C.C(N(CC)CC)C.[O:45]1CCC[CH2:46]1>>[CH:46]([C:26]1[CH:27]=[N:28][C:19]([C:10]2[NH:9][C:13](=[O:14])[C:12]([CH:16]([CH3:17])[CH3:18])([CH3:15])[N:11]=2)=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22])=[O:45]Participants
Reactant 4
Product 1
Procedure
A stirred solution of 1.38 g of 2-(1-benzoyl-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-(dibromomethyl)nicotinic acid, methyl ester, in 35 mL tetrahydrofuran is cooled to -78° and treated with a mixture of 0.3 mL of N-ethylethylenediamine, 10 mL tetrahydrofuran, and 0.8 mL of triethylamine. After warming to room temperature, the reaction solution is treated with 0.3 mL of N-ethylethylenediamine, stirred for 2 hours, heated at reflux for 24 hours, and concentrated in vacuo. The residue is partitioned between methylene chloride and water; the aqueous phase is further extracted with methylene chloride, and the combined organic phases are dried and concentrated in vacuo. Chromatography of the residue on silica gel using hexane-ethyl acetate mixtures affords the desired product, mp 113°-117°.
Workup
- temperatureheated
- temperatureat reflux for 24 hours
- concentrationconcentrated in vacuo
- customThe residue is partitioned between methylene chloride and water
- extractionthe aqueous phase is further extracted with methylene chloride
- customthe combined organic phases are dried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-99ab6b35aaf0408391f731c883836ce4
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05334576
Reaction notes
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