Methanol → HCID 178479688, compound

To a mixture of 5-amino-4,5,6,7-tetrahydro-1H-benzimidazole, dihydrochloride (420 mg, 2.0 mmol) and DMA (10 ml), 5.4 M NaOMe in MeOH (0.74 ml, 4.0 mmol) was added. triethylamine (0.276 ml, 2 mmol) was added followed by dropwise addition of 5-cyclohexylpentanoic acid chloride (609 mg, 3.0 mmol). When addition was complete the mixture was stirred at ambient temperature for 30 min and then heated at 80° C. for 1 hour and finally allowed to cool to ambient temperature within 1 hour. The volatiles were evaporated and the residue was stirred vigorously with a mixture of H2O (100 ml), 1 N hydrochloric acid (10 ml) and diethyl ether (50 ml). The phases were separated and the aqueous phase was washed with diethyl ether (2×50 ml) and then made alkaline to pH 10-11 with 4 N sodium hydroxide. The alkaline mixture was extracted with ethyl acetate (2×50 ml) and the organic extracts were evaporated in vacuo. The residue was dissolved in 1 N hydrochloric acid and evaporated to dryness. The residue was re-evaporated with acetone to give 260 mg (38%) of the title compound.

1. additionwas added
2. additionWhen addition
3. temperatureheated at 80° C. for 1 hour
4. temperatureto cool to ambient temperature within 1 hour
5. customThe volatiles were evaporated
6. stirringthe residue was stirred vigorously with a mixture of H2O (100 ml), 1 N hydrochloric acid (10 ml) and diethyl ether (50 ml)
7. customThe phases were separated
8. washthe aqueous phase was washed with diethyl ether (2×50 ml)
9. extractionThe alkaline mixture was extracted with ethyl acetate (2×50 ml)
10. customthe organic extracts were evaporated in vacuo
11. dissolutionThe residue was dissolved in 1 N hydrochloric acid
12. customevaporated to dryness
13. customThe residue was re-evaporated with acetone

ORD record

ord-ddf120838f83434bb9c46b33312d27a7

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437147B1