Isopropanol → N-(2-diethylaminoethyl)-6-chloro-5-ethylamino-3-methoxypyrazine-2-carboxamide
Reaction equation
C(O)(C)C.[Cl:5][C:6]1[N:11]=[C:10]([C:12]([O:14]C)=O)[C:9]([O:16][CH3:17])=[N:8][C:7]=1[NH:18][CH2:19][CH3:20].[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][NH2:26])[CH3:22]>CCOCC>[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][NH:26][C:12]([C:10]1[C:9]([O:16][CH3:17])=[N:8][C:7]([NH:18][CH2:19][CH3:20])=[C:6]([Cl:5])[N:11]=1)=[O:14])[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In 14 ml. of isopropyl alcohol were dissolved 1.4 g. of methyl 6-chloro-5-ethylamino-3-methoxypyrazine-2-carboxylate and 1.4 g. of N,N-diethylethylenediamine and the solution was refluxed for 4 days. After the reaction was over, the solvent was distilled off under reduced pressure from the reaction mixture and the residue obtained was applied to a silica gel column chromatography. The column was then developed using a mixture of ether and N-hexane of 1:1 volume ratio as an eluting solution. From the 1st fraction 0.7 g. of methyl 5-ethylamino-6-chloro-3-methoxypyrazine-2-carboxylate used as the starting material was recovered and from the 2nd fraction 0.7 g. of colorless plate crystals of N-(2-diethylaminoethyl)-6-chloro-5-ethylamino-3-methoxypyrazine-2-carboxamide a melting at 142° C. were obtained. The product obtained by recrystallizing the crystals from a mixture of benzene and n-hexane melted at 142° C.
Workup
- distillationwas distilled off under reduced pressure from the reaction mixture
- customthe residue obtained
- customwas recovered and from the 2nd fraction 0.7 g
Sources & evidence
- ORD record
- ord-e6ba23b8a2444e7e99d45698f22728de
- Source dataset
- uspto-grants-1977_08
- Patent number
- US04041032
Reaction notes
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