Reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][NH2:9])[N:5]=[CH:4][N:3]=1.CN(C)[CH:12]=[C:13]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:14](OCC)=[O:15].C(O)(=[O:28])C>>[OH:28][C:2]1[N:3]=[CH:4][N:5]=[C:6]([N:8]2[C:14](=[O:15])[C:13]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:12][NH:9]2)[CH:7]=1Participants
Procedure
For 16 h, 2.8 g (19.6 mmol) of the compound from Example 7A and 4.3 g (19.6 mmol) of the compound from Example 3A are stirred in 50 ml of glacial acetic acid at boiling point (bath temperature 125° C.). For work-up, the resulting precipitate is filtered off, the filter residue is washed with diethyl ether and the filtrate is concentrated on a rotary evaporator. The filter residue is dissolved in 50 ml of ethanol, 18.5 ml (2.7 g, 39.2 mmol) of 21% strength ethanolic sodium methoxide solution are added and the solution is stirred at RT for 16 h. The reaction mixture is then adjusted to pH 5 using 1 N hydrochloric acid and stirred at RT for 2 h, the precipitate is then filtered off, the filter residue is washed with water and ethanol and the product is dried under reduced pressure.
Workup
- filtrationFor work-up, the resulting precipitate is filtered off
- washthe filter residue is washed with diethyl ether
- concentrationthe filtrate is concentrated on a rotary evaporator
- dissolutionThe filter residue is dissolved in 50 ml of ethanol
- addition18.5 ml (2.7 g, 39.2 mmol) of 21% strength ethanolic sodium methoxide solution are added
- stirringstirred at RT for 2 h
- filtrationthe precipitate is then filtered off
- washthe filter residue is washed with water and ethanol
- customthe product is dried under reduced pressure
Sources & evidence
- ORD record
- ord-9ca9be7b4b844636ba5b04cd221d2e6d
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524699B2
Linked notes
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