Pyridine → HCID 54501726, compound
Reaction equation
[N:1]1[CH:6]=CC=C[CH:2]=1.Cl.C([C:11]1[N:15]2[CH2:16][CH2:17][CH2:18][N:19]=[C:14]2SC=1C(Cl)=O)CC.C(S(C1C=CC(N)=CC=1)(=O)=O)CCCCCC>CN(C)C=O>[CH3:11][NH:15][C:16]1[CH:2]=[N:1][CH:6]=[C:18]([NH:19][CH3:14])[CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In the mixture of 50 ml of pyridine and 5 ml of dimethylformamide was suspended 1.04 g of 3-propyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonyl-chloridehydrochloride (described in Example 13). To the suspension was added 940 mg of 4-n-heptylsulfonylaniline obtained in Reference Example 7, and 45 mg of 3,5-dimethylaminopyridine, followed by stirring at 70° C. for 17 hours. The reaction mixture was concentrated and to the concentrate was added saturated sodium hydrogencarbonate aqueous solution. The mixture was extracted with chloroform. The extract was washed with saturated sodium chloride aqueous solution and dried over anhydrous potassium carbonate. The solvent was removed under reduced pressure. The residue was dissolved in ethanol. To the mixture was added saturated hydrogenchloride diethylether solution, followed by stirring at room temperature. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol (10:1 by volume). To the resulting substance was added saturated hydrogenchloride diethylether solution. The solvent was removed under reduced pressure. The residue was recrystallized from methanol-diethylether to obtain 559 mg of the titled compound.
Sources & evidence
- ORD record
- ord-36c20f9e02624aafbe3c4d85a5e8ccea
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05599813
Reaction notes
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