Diethylamine → HCID 13784174, compound
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[C:18]([NH:20][CH2:21][CH3:22])[C:17]([C:23]([OH:25])=O)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([N:28](CC)[CH2:29][CH3:30])[CH3:27].S(Cl)(Cl)=O.C(NCC)C>O.C(Cl)(Cl)Cl>[CH2:26]([N:28]([CH2:29][CH3:30])[C:23]([C:17]1[C:18]([NH:20][CH2:21][CH3:22])=[N:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10]2)=[N:15][CH:16]=1)=[O:25])[CH3:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 0.5 g (1.46 mmol) of 2-(4-benzylpiperazino)-4-ethylaminopyrimidine-5-carboxylic acid (the compound synthesized in Referential Example 67) and 20 ml of chloroform was added with 0.2 ml (1.43 mmol) of triethylamine, followed by a further addition of 0.22 ml (3.02 mmol) of thionyl chloride. The resultant mixture was stirred at room temperature for 1 hour. After adding 1.0 ml (9.67 mmol) of diethylamine and stirring the resultant mixture for 1 hour, water was added. The resultant mixture was extracted with chloroform. After drying the chloroform layer with MgSO4, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain 0.37 g of the above-identified compound (yield: 64%).
Workup
- extractionThe resultant mixture was extracted with chloroform
- dry with materialAfter drying the chloroform layer with MgSO4
- distillationthe solvent was distilled off under reduced pressure
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-f0fa1f0de66f4f3d99680e1d69ef77c9
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04734418
Reaction notes
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