4-methylhexan-2-amine

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

Procedure: Starting from 3,7-dichloro-4H-1,2,4-benzothiadiazine 1,1-dioxide (500 mg; 1.99 mmol) and 1,3-dimethylpentylamine (1 g; 8.68 mmol) and with the use of same procedure as in example 21 230 mg (35.1%) of the title compound was prepared; m.p. >220° C.; 1H-NMR (DMSO-d6) ppm; 10.41 (s, 1H, NH), 7.68 (d, 1H, H-8), 7.60 (dd, 1H, H-5), 7.2 (d, 1H, H-7), 7.0 (br, 1H, NH), 3.95 (m, 1H, CH), 1.5 (m, 8H), 0.9 (m, 6H, 2×CH3); MS:EI/70eV: 329 (M+), 301, 258, 231, 190, 126, 69, 44. Analysis: C14H20ClN3O2S requires C, 50.98; H, 6.11; N, 12.74; (found C, 51.23; H, 6.42; N, 12.53).

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

Procedure: 2′-Methyl-5′-(5-methyl-1,3,1-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (11.3 mg, 0.034 mmol), HOBT (6.0 mg, 0.044 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (8.0 mg, 0.042 mmol) and 1,3-dimethylpentylamine (0.34 mmol) were mixed in DMF (0.7 ml) and the reaction left at room temperature for 18 h. The DMF was evaporated under vacuum and the residue partitioned between DCM (0.4 ml) and water (0.4 ml). The organic phase was washed with aqueous sodium hydroxide (0.5M, 0.2 ml) and the DCM evaporated under vacuum. The residue was purified by mass directed HPLC to give N-(1,3-dimethylpentyl)-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide. The DMF was evaporated under vacuum the residue partitioned between DCM (0.4 ml) and water (0.4 ml) The organic phase was washed with aqueous sodium hydroxide (0.5M, 0.2 ml) the DCM evaporated under vacuum The residue was purified by mass

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

Procedure: Starting from 3,7-dichloro-4H-1,2,4-benzothiadiazine 1,1-dioxide (500 mg; 1.99 mmol) and 1,3-dimethylpentylamine (1 g; 8.68 mmol) and with the use of same procedure as in example 21 230 mg (35.1%) of the title compound was prepared; m.p. >220° C.; 1H-NMR (DMSO-d6) ppm; 10.41 (s, 1H, NH), 7.68 (d, 1H, H-8), 7.60 (dd, 1H, H-5), 7.2 (d, 1H, H-7), 7.0 (br, 1H, NH), 3.95 (m, 1H, CH), 1.5 (m, 8H), 0.9 (m, 6H, 2×CH3); MS:EI/70eV: 329 (M+), 301, 258, 231, 190, 126, 69, 44. Analysis: C14H20ClN3O2S requires C, 50.98; H, 6.11; N, 12.74; (found C, 51.23; H, 6.42; N, 12.53).