Hydrochloric Acid → 4-[5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-N-methylnicotinamido]butyric acid
Reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:11](=[O:12])[N:10]3[C:13](=[O:20])[C:14]([CH:17]([CH3:19])[CH3:18])([CH3:16])[N:15]=[C:9]3[C:6]2=[N:7][CH:8]=1)[CH3:2].Cl.[CH3:22][NH:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].C(N(CC)CC)C.Cl>CN(C)C=O.O>[CH2:1]([C:3]1[CH:8]=[N:7][C:6]([C:9]2[NH:10][C:13](=[O:20])[C:14]([CH:17]([CH3:19])[CH3:18])([CH3:16])[N:15]=2)=[C:5]([CH:4]=1)[C:11]([N:23]([CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH3:22])=[O:12])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A stirred solution of 7-ethyl-2-isopropyl-2-methyl-5H-imidazo[1′,2′:1,2]pyrrolo[3,4-b]pyridine-3(2H),5-dione (5.47 g, 20.19 mmol) in anhydrous N,N-dimethylformamide is treated successively with 4-(methylamino)butyric acid hydrochloride (3.29 g, 21.2 mmol) and triethylamine (4.29 g, 42.39 mmol). The resulting mixture is stirred at room temperature under nitrogen for 2.5 hours. After this period, the reaction mixture is diluted with water, acidified with concentrated hydrochloric acid and extracted with ether. The organic extract is dried over magnesium sulfate, vacuum filtered through diatomaceous earth and concentrated in vacuo to give the title product as a white solid, mp 42-49° C. (dec.).
Workup
- waitAfter this period
- extractionextracted with ether
- extractionThe organic extract
- dry with materialis dried over magnesium sulfate, vacuum
- filtrationfiltered through diatomaceous earth
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b70d557e792544e6b2419375958e43e6
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06407217B1
Reaction notes
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