Acetamidine monohydrochloride → 2-Chloro-5-fluoro-N-(4,6-dihydroxy-2-methyl-pyrimidin-5-yl)-benzamide
Reaction equation
C[O-].[Na+].Cl.[C:5]([NH2:8])(=[NH:7])[CH3:6].C([O:11][C:12](=O)[CH:13]([NH:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[Cl:28])[C:14](OCC)=[O:15])C>C(O)C>[Cl:28][C:22]1[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=1[C:20]([NH:19][C:13]1[C:12]([OH:11])=[N:7][C:5]([CH3:6])=[N:8][C:14]=1[OH:15])=[O:29]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
1.5 equivalents of sodium methoxide (30% in methanol) were added to a suspension of 13.4 g of acetamidine hydrochloride in 150 ml of ethanol. The precipitate was filtered off and washed with 100 ml of ethanol. Additional 1.5 equivalents of sodium methoxide (30% in methanol) were added to the filtrate. Then a solution of 39.3 g of 2-(2-chloro-5-fluoro-benzoylamino)malonic acid diethyl ester in 100 ml of ethanol was added dropwise. The reaction mixture was stirred at 60° C. for 2 h. After cooling to 0° C. for 30 min, the precipitate was filtered off with suction, washed with 100 ml of a solution of hydrogen chloride in isopropanol and dried to give 35.7 g of the title compound.
Workup
- filtrationThe precipitate was filtered off
- washwashed with 100 ml of ethanol
- temperatureAfter cooling to 0° C. for 30 min
- filtrationthe precipitate was filtered off with suction
- washwashed with 100 ml of a solution of hydrogen chloride in isopropanol
- customdried
Sources & evidence
- ORD record
- ord-9f3e932a474a4eabbf876b5fa275f9e8
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08735387B2
Reaction notes
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