O-butylhydroxylamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reaction of the isothiourea dihydrochloride of Example 1 (i) with n-propoxyamine and n-butyoxyamine according to the procedure of Example 1 (ii) gave respectively N-methyl-N'-n-propoxy-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochloride and N-methyl-N'-n-butoxy-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reaction of the isothiourea dihydrochloride of Example 1 (i) with n-propoxyamine and n-butyoxyamine according to the procedure of Example 1 (ii) gave respectively N-methyl-N'-n-propoxy-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochloride and N-methyl-N'-n-butoxy-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 424 (100 mg, 0.25 mmol) and O-butyl-hydroxylamine (63 mg, 0.50 mmol) were treated as described for compound 337. Flash chromatography (ethyl acetate/petroleum ether: graduated from 20/80 to 60/40) provided the title compound. 13C NMR (CDCl3) δ 195.4, 165.9, 159.3 (dd), 155.7 (dd), 148.3, 142.0, 139.8, 135.4, 133.8, 131.7, 129.5, 129.1, 128.6, 127.7, 124.6 (dd), 124.1 (dd), 116.2, 112.8, 111.7 (dd), 105.0 (dd), 76.9, 30.1, 20.4, 19.1, 13.8

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 424 (100 mg, 0.25 mmol) and O-butyl-hydroxylamine (63 mg, 0.50 mmol) were treated as described for compound 337. Flash chromatography (ethyl acetate/petroleum ether: graduated from 20/80 to 60/40) provided the title compound. 13C NMR (CDCl3) δ 195.4, 165.9, 159.3 (dd), 155.7 (dd), 148.3, 142.0, 139.8, 135.4, 133.8, 131.7, 129.5, 129.1, 128.6, 127.7, 124.6 (dd), 124.1 (dd), 116.2, 112.8, 111.7 (dd), 105.0 (dd), 76.9, 30.1, 20.4, 19.1, 13.8

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The present compound was synthesized by a method similar to that in Example 187 and using 6-chloro-1-oxo-4-phenyl-1H-isochromen-3-carboxylic acid and O-n-butylhydroxylamine. A colorless powder (280 mg). The present compound was synthesized by a method similar to that in Example 187

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6-chloro-1-oxo-4-phenyl-1H-isochromen-3-carboxylic acid (210 mg), O-n-butylhydroxylamine (620 mg) and ethanol (8.4 ml) was stirred for 12 hrs. at 90° C. in a sealed tube. After cooling, the reaction mixture was concentrated under reduced pressure to give 2-butoxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid. at 90° C. After cooling the reaction mixture was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6-chloro-1-oxo-4-phenyl-1H-isochromen-3-carboxylic acid (210 mg), O-n-butylhydroxylamine (620 mg) and ethanol (8.4 ml) was stirred for 12 hrs. at 90° C. in a sealed tube. After cooling, the reaction mixture was concentrated under reduced pressure to give 2-butoxy-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid. at 90° C. After cooling the reaction mixture was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reaction of the isothiourea dihydrochloride of Example 1 (i) with n-propoxyamine and n-butyoxyamine according to the procedure of Example 1 (ii) gave respectively N-methyl-N'-n-propoxy-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochloride and N-methyl-N'-n-butoxy-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine dihydrochloride.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir: