Formaldehyde → HCID 57585127, compound

Participants

Reaction Steps

A suspension of N-(6-(5-amino-6-chloropyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (500 mg, 1568 μmol) and NaBH4 (500 mg, 13216 μmol) in THF (4 mL) was cooled with an ice bath. A cold mixture of formaldehyde (700 μL, 9325 μmol) and H2SO4 (3000 μl, 9000 μmol) was added slowly. More formaldehyde (700 μL, 9325 μmol) was added followed by the addition of NaCNBH3 (excess). The mixture was neutralized with Na2CO3 and the mixture was aged at 40° C. for 2 h. After standing overnight at rt, the mixture was filtered, washed with H2O, and air dried. The mixture was suspended in pyridine (10 mL) and was treated with HCl (conc., 20 mL). The mixture was filtered, the residue was washed with HCl (5 N). The filtrate was neutralized with NaOH (5N) and Na2CO3. The resulting slurry was aged overnight. The slurry was filtered, washed with H2O, and air dried. The solid was suspended in hot DMSO (10 mL), diluted with hot H2O (10 mL), and filtered. The solid was air dried over the weekend to give the product as a green powder (180 mg). MS (ESI, pos. ion) m/z: calc'd for C16H15ClN4OS: 346.0. found: 347.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.22 (s, 3H) 2.86 (s, 6H) 7.74-7.89 (m, 3H) 8.38 (d, J=21.13 Hz, 2H) 12.43 (s, 1H).

Provenance & Evidence