Acetic Acid → HCID 22283216, compound

Temperature

20 °C

To a suspension of 2-amino-4-methoxy-benzothiazole-7-carbaldehyde (440 mg, 2.1 mmol) in THF (100 ml) was added morpholine (276 mg, 3.2 mmol), acetic acid (190 mg, 3.2 mmol) followed by NaBH(OAc)3 (672 mg, 3.2 mmol). This mixture was stirred vigorously at 20° C. for 48 hours, after which time water (50 ml) and 5% NaHCO3 solution (50 ml) were added and the mixture agitated vigorously. After separating the organic and aqueous layers, the aqueous phase was extracted with EtOAc (50 ml) and the combined organic phase was washed with saturated NaCl solution (100 ml) then dried with Na2SO4, filtered and evaporated. The solid residue was suspended in ether (20 ml) and filtered then the filter cake was washed with ether (10 ml), and dried under vacuum (0.05 mmHg, 50° C.) to afford the title compound as a yellow solid (430 mg, 73% yield), MS: m/e=280.2 (M+).

1. stirringthe mixture agitated vigorously
2. customAfter separating the organic and aqueous layers
3. extractionthe aqueous phase was extracted with EtOAc (50 ml)
4. washthe combined organic phase was washed with saturated NaCl solution (100 ml)
5. dry with materialthen dried with Na2SO4
6. filtrationfiltered
7. customevaporated
8. filtrationfiltered
9. washthe filter cake was washed with ether (10 ml)
10. customdried under vacuum (0.05 mmHg, 50° C.)

ORD record

ord-ed41b1303dac4551ac5e8fbba272a61e

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06835732B2