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With isopentyl nitrite; In tetrahydrofuran; for 4.0h;Heating / reflux;
Isoamyl nitrite (22.0 mmol) is added to a solution of 2-amino-benzothiazole-7-carboxylic acid methyl ester (10.1 mmol) in THF (29 mL). The mixture is heated to reflux for 4h, the solvents are removed in vacuo and the residue is purified by flash chromatography <n="80"/>(gradient: heptane to EtOAc/heptane 4/6) to give the desired product. LC-MS: tR = 0.85 min; [M+H]+ = 194.0.
With isopentyl nitrite; In tetrahydrofuran; for 4.0h;Heating / reflux;
Isoamyl nitrite (22.0 mmol) is added to a solution of 2-amino-benzothiazole- 7-carboxylic acid methyl ester (10.1 mmol) in THF (29 mL). The mixture is heated to reflux for 4h, the solvents are removed in vacuo and the residue is purified by FC (gradient: heptane to EtO Ac/heptane 4/6) to give the desired product. LC-MS: tR = 0.85 min; [M+H]+ = 194.0.
With isopentyl nitrite; In tetrahydrofuran; for 4.0h;Reflux;
A.4.3 Synthesis of benzothiazole-7-carboxylic acid methyl ester; Isoamyl nitrite (22.0 mmol) is added to a solution of 2-amino-benzothiazole-7-carboxylic acid methyl ester (10.1 mmol) in THF (29 mL). The mixture is heated to reflux for 4h, the solvents are removed in vacuo and the residue is purified by flash chromatography (gradient: heptane to EtOAc/heptane 4/6) to give the desired product. LC-MS: tR = 0.85 min; [M+H]+ = 194.0.
At 00C an aqueous NaOH solution (50%, 6.0 rnL) is added to a solution of benzothiazole- 7-carboxylic acid methyl ester in a mixture of MeOH (39 mL), THF (11.7 mL) and water (3.0 mL). The mixture is stirred for 4h and concentrated in vacuo. At 00C water (60 mL) is added and the mixture is made acidic (pH 5) by addition of cone, hydrochloric acid. After 30 min the precipitate is filtered off, washed with water and dried in vacuo to give the desired product. LC-MS : tR = 0.77 min; [M+CH3CN+H]+ = 221.1.
A.4.4 Synthesis of benzothiazole-7-carboxylic acid; At 00C an aq. NaOH solution (50%, 6.0 mL) is added to a solution of benzothiazole-7- carboxylic acid methyl ester in a mixture of MeOH (39 mL), THF (11.7 mL) and water (3.0 mL). The mixture is stirred for 4h and concentrated in vacuo. At 00C water (60 mL) is added and the mixture is made acidic (pH 5) by addition of cone, hydrochloric acid. After <n="61"/>30 min the precipitate is filtered off, washed with water and dried in vacuo to give the desired product. LC-MS: tR = 0.77 min; [M+CH3CN+H]+ = 221.1.
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