3-methylbutan-2-amine;hydrochloride

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

Procedure: The title compound was prepared from 6-chloro-2,3-dihydro-3-oxo-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide (4.94 g, 15.84 mmol) and 1,2-dimethylpropylamine hydrochloride (8.0 g, 65.0 mmol) by a method analogous to the method described in example 37, except that the product was purified by column chromatography affording 143 mg (2.4%) of pure product; m.p. (DSC) 244° C. (methanol); 1H-NMR (DMSO-d6): δ 0.90 (dd, 6H, CH(CH3)2), 1.11 (d, 3H, NCHCH3), 1.76 (m, 1H, CH(CH3)2), 3.71 (m, 1H, NHCH), 7.34 (br., 1H, NH), 7.41 (br.s, 1H, ArH), 7.80 (br.s, 2H, SO2NH2), 8.18 (s, 1H, ArH), 10.58 (br.s, 1H, NH); MS (FAB): m/e 381/383 (MH+); (C12H17N4Cl1O4S2) calc. C, 37.84; H, 4.50; N, 14.71; found C, 37.66; H, 4.65; N, 14.52. was purified by column chromatography

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

Procedure: The title compound was prepared from 6-chloro-2,3-dihydro-3-oxo-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide (4.94 g, 15.84 mmol) and 1,2-dimethylpropylamine hydrochloride (8.0 g, 65.0 mmol) by a method analogous to the method described in example 37, except that the product was purified by column chromatography affording 143 mg (2.4%) of pure product; m.p. (DSC) 244° C. (methanol); 1H-NMR (DMSO-d6): δ 0.90 (dd, 6H, CH(CH3)2), 1.11 (d, 3H, NCHCH3), 1.76 (m, 1H, CH(CH3)2), 3.71 (m, 1H, NHCH), 7.34 (br., 1H, NH), 7.41 (br.s, 1H, ArH), 7.80 (br.s, 2H, SO2NH2), 8.18 (s, 1H, ArH), 10.58 (br.s, 1H, NH); MS (FAB): m/e 381/383 (MH+); (C12H17N4Cl1O4S2) calc. C, 37.84; H, 4.50; N, 14.71; found C, 37.66; H, 4.65; N, 14.52. was purified by column chromatography

Conditions: temp:195.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phosphorus pentoxide (7.55 g, 53.2 mmol), N,N-dimethylcyclohexylamine (17 ml, 113 mmol) and 1,2-dimethylpropylamine hydrochloride (12.4 g, 100.4 mmol) were carefully mixed and heated with mechanical stirring on an oil bath at 190-200° C. for about 15 min. To the homogeneous mass was added 6-chloro-3,4-dihydro-3-oxo-1,2,4-benzothiadiazine 1,1-dioxide (5.84 g, 25.1 mmol) and the mixture was stirred at 235° C. for 2 h. After cooling to about 100° C., water (200 ml) was added and the dark mixture was hydrolysed by stirring over night at room temperature. The precipitate was isolated by filtration and recrystallised from ethanol with decolorising charcoal to give 2,83 g (37%) of the pure title compound; m.p. (DSC) 264.7° C.; 1H-NMR (DMSO-d6): δ 0.90 (dd, 6H, CH(CH3)2), 1.09 (d, 3H, NCHCH3), 1.76 (m, 1H, CH(CH3)2), 3.70 (m, 1H, NHCH), 7.15 (br., 1H, NH), 7.28 (m, 2H, ArH), 7.68 (d, 1H, ArH), 10.3 (br.s, 1H, NH); (C12H16N3Cl1O2S1) calc. C, 47.76; H, 5.34; N 13.92; found C, 47.66; H, 5.47; N, 13.91. heated the mixture was stirred at 235° C. for 2 h After cooling to about 100° C. by stirring over night at room temperature The precipitate was isolated by filtration recrystallised from ethanol with decolorising charcoal

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phosphorus pentoxide (2.84 g; 20 mmol), N,N-dimethylcyclohexylamine (5 ml, 33 mmol) and 1,2-dimethylpropylamine hydrochloride (2.47 g; 20 mmol) were carefully mixed in a three necked flask equipped with mechanical stirring and condenser with drying tube. The mixture was heated on an oil bath at 200° C. until a homogeneous mass was obtained. Then 6-chloro-2,3-dihydro-3-oxo-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (1.2 g; 5 mmol) was added and the mixture was stirred at 240° C. for 45 min. The mixture was allowed to cool to about 100° C., 150 ml of water was added and stirring was continued at ambient temperature for approximately 1 h. The hydrolysed mixture was filtered and the dark precipitate was washed with water and dissolved in boiling ethanol, treated with charcoal, filtered and finally evaporated to dryness. Flash chromatography (ethyl acetate/silica gel) afforded 105 mg (7%) of the pure title compound; m.p. 216°-218° C.; 1H-NMR (DMSO-d6): δ 0.90 (d, 6H, CH(CH3)2), 1.08 (d, 3H, NCHCH3), 1.75 (m, 1H, CH(CH3)2), 3.65 (m, 1H, NHCH), 7.11 (br. s, 2H, 5-H+NH), 10.68 (s, 1H, NH); MS m/e: 307/309 (M+). equipped condenser with drying tube was obtained the mixture was stirred at 240° C. for 45 min to cool to about 100° C. stirring The hydrolysed mixture was filtered the dark precipitate was washed with water dissolved treated with charcoal filtered finally evaporated to dryness

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

Procedure: The title compound was prepared from 6-chloro-2,3-dihydro-3-oxo-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide (4.94 g, 15.84 mmol) and 1,2-dimethylpropylamine hydrochloride (8.0 g, 65.0 mmol) by a method analogous to the method described in example 37, except that the product was purified by column chromatography affording 143 mg (2.4%) of pure product; m.p. (DSC) 244° C. (methanol); 1H-NMR (DMSO-d6): δ 0.90 (dd, 6H, CH(CH3)2), 1.11 (d, 3H, NCHCH3), 1.76 (m, 1H, CH(CH3)2), 3.71 (m, 1H, NHCH), 7.34 (br., 1H, NH), 7.41 (br.s, 1H, ArH), 7.80 (br.s, 2H, SO2NH2), 8.18 (s, 1H, ArH), 10.58 (br.s, 1H, NH); MS (FAB): m/e 381/383 (MH+); (C12H17N4Cl1O4S2) calc. C, 37.84; H, 4.50; N, 14.71; found C, 37.66; H, 4.65; N, 14.52. was purified by column chromatography

Conditions: temp:195.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phosphorus pentoxide (7.55 g, 53.2 mmol), N,N-dimethylcyclohexylamine (17 ml, 113 mmol) and 1,2-dimethylpropylamine hydrochloride (12.4 g, 100.4 mmol) were carefully mixed and heated with mechanical stirring on an oil bath at 190-200° C. for about 15 min. To the homogeneous mass was added 6-chloro-3,4-dihydro-3-oxo-1,2,4-benzothiadiazine 1,1-dioxide (5.84 g, 25.1 mmol) and the mixture was stirred at 235° C. for 2 h. After cooling to about 100° C., water (200 ml) was added and the dark mixture was hydrolysed by stirring over night at room temperature. The precipitate was isolated by filtration and recrystallised from ethanol with decolorising charcoal to give 2,83 g (37%) of the pure title compound; m.p. (DSC) 264.7° C.; 1H-NMR (DMSO-d6): δ 0.90 (dd, 6H, CH(CH3)2), 1.09 (d, 3H, NCHCH3), 1.76 (m, 1H, CH(CH3)2), 3.70 (m, 1H, NHCH), 7.15 (br., 1H, NH), 7.28 (m, 2H, ArH), 7.68 (d, 1H, ArH), 10.3 (br.s, 1H, NH); (C12H16N3Cl1O2S1) calc. C, 47.76; H, 5.34; N 13.92; found C, 47.66; H, 5.47; N, 13.91. heated the mixture was stirred at 235° C. for 2 h After cooling to about 100° C. by stirring over night at room temperature The precipitate was isolated by filtration recrystallised from ethanol with decolorising charcoal