Chloroform → HCID 131715687, compound
Reaction equation
C[N:2]1[CH:11]2[C:6]([C:7]3[N:14]=[C:13]([NH:15]C(=O)C(C)C)[S:12][C:8]=3[CH2:9][CH2:10]2)=[CH:5][CH2:4][CH2:3]1.N#CBr.C(Cl)(Cl)[Cl:25]>>[ClH:25].[ClH:25].[N:14]1[C:7]2[C:6]3[CH:11]([CH2:10][CH2:9][C:8]=2[S:12][C:13]=1[NH2:15])[NH:2][CH2:3][CH2:4][CH:5]=3Participants
Procedure
A solution of 5.00 g (17.15 mmol) of (±) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolo[4,5-f]quinolin-2-yl)-2-methylpropanamide (Example 15) in 150 ml of chloroform containing 20.6 ml (19.25 mmol) of a 1.07 M solution of cyanogen bromide in chloroform is refluxed, under nitrogen, for 12 hours. The solution is concentrated and the resultant yellow oily solid is refluxed in 150 ml of 10% hydrochloric acid for 12 hours. The solution is cooled, basified with ammonium hydroxide and extracted into chloroform. The chloroform extract is dried (magnesium sulfate), filtered and concentrated to a brown oil. Medium pressure chromatography (silica gel, 5% methanol--2% ammonium hydroxide--93% ethyl acetate) followed by salt formation and recrystallization from methanol/diethyl ether affords the title compound as a tan solid; mp 277°-279° C. (dec.).
Workup
- concentrationThe solution is concentrated
- temperaturethe resultant yellow oily solid is refluxed in 150 ml of 10% hydrochloric acid for 12 hours
- temperatureThe solution is cooled
- extractionextracted into chloroform
- extractionThe chloroform extract
- dry with materialis dried (magnesium sulfate)
- filtrationfiltered
- concentrationconcentrated to a brown oil
- customMedium pressure chromatography (silica gel, 5% methanol--2% ammonium hydroxide--93% ethyl acetate) followed by salt formation and recrystallization from methanol/diethyl ether
Sources & evidence
- ORD record
- ord-6afd7c67cfa845f882ae6e835487c57c
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04762843
Reaction notes
Loading…