6-METHOXY-N-(PYRIDIN-3-YLMETHYL)-1,3-BENZOTHIAZOL-2-AMINE synthesis

Yield:16763-15-8 36%

Reaction Conditions:

Stage #1: 3-pyridinecarboxyaldehyde;6-methoxybenzo[d]thiazol-2-amine in toluene at 110; for 16 h;Molecular sieve;
Stage #2: with sodium tetrahydridoborate;ethanol in toluene at 110; for 2 h;

Steps:

3.1; 21.1; 35.1 Step 1: Preparation of 6-methoxy-N-(pyridin-3-ylmethyl)benzo[d]thiazol-2-amine

To a solution of nicotinaldehyde (1.19 g, 11 mmol), 6-methoxybenzo[d]thiazol-2-amine (2.00 g, 11 mmol) in toluene (10 mL) was added dried 4 ? molecular sieves. The mixture was heated to 110 °C and stirred for 16 hours. Then a solution of sodium borohydride (2.11 g, 56 mmol) in ethanol (20 mL) was added. The reaction was stirred at 110 °C for 2 hours. The reaction was filtered over Celite and the solvent was removed under the reduced pressure. Crude product was further purified by silica gel column in a gradient 0-5% methanol in dichloromethane to offer 6-methoxy-N-(pyridin-3-ylmethyl)benzo[d]thiazol- 2-amine (1.10 g, 4.1 mmol, 36%) as a white solid. LCMS (ESI) m/z: 272.1 [M+H]⁺.

References:

WO2021/247921,2021,A1 Location in patent:Page/Page column 56-57; 71; 82