Hydrochloric Acid → HCID 178461360, compound
Reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([OH:12])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29][CH2:28]1.C(N(CC)C(C)C)(C)C.Cl>CN(C)C=O>[CH3:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([NH:33][C:10]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[O:12])[CH2:29][CH2:28]1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of benzothiazole-2-carboxylic acid (359 mg, 2 mmol), and 1,1′-carbonyldiimidazole (325 mg, 2 mmol) in dimethylformamide (4 mL) was heated at 50° C. for 1 hour. After this time, trans-4-methylcyclohexylamine hydrochloride (300 mg, 2 mmol), and N,N-diisopropylethylamine (0.525 mL, 3 mmol) were added and the mixture heated at 50° C. for 3 hours. The reaction mixture was cooled, and treated with 10% HCl (15 mL). The solution was extracted with ethyl acetate (15 mL). The ethyl acetate extract was then washed with 10% HCl (15 mL), water (15 mL), and brine (15 mL). Dilution of the remaining solution with ethyl acetate (50 mL) and cooling to −20° C. afforded 25 mg (5%) 412:
Workup
- temperatureThe reaction mixture was cooled
- extractionThe solution was extracted with ethyl acetate (15 mL)
- extractionThe ethyl acetate extract
- washwas then washed with 10% HCl (15 mL), water (15 mL), and brine (15 mL)
- temperatureDilution of the remaining solution with ethyl acetate (50 mL) and cooling to −20° C.
Sources & evidence
- ORD record
- ord-e42e214bf6664340a346a1192bf3770a
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06429207B1
Reaction notes
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