Acetic Acid → HCID 67194681, compound

2-Bromo-5-formylthiazole (198 mg, 1.034 mmol, available from Fluorochem) was mixed with acetic acid (0.148 mL, 2.58 mmol) and Piperidine (0.128 mL, 1.292 mmol), dissolved in Dichloromethane (DCM) (9.5 mL) and stirred under nitrogen for 30 minutes. sodium triacetoxyborohydride (411 mg, 1.938 mmol) was added and the reaction was allowed to stir under nitrogen for 45 minutes. A second sample of sodium triacetoxyborohydride (411 mg, 1.938 mmol) was added and the reaction was left to stir under nitrogen for 4.5 days. The reaction was loaded onto a 5 g SCX-column, eluting with MeOH (40 mL) followed by 2M MeOH/NH3 (40 mL). Product-containing fractions were evaporated to dryness to give a yellow solid. This was partitioned between sodium bicarbonate (20 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (70 mL) and the organic fractions were combined, washed (brine (50 mL)), dried (sodium sulfate), filtered and evaporated to dryness to give a yellow solid (214 mg). This was purified on a 25+S Biotage silica column, eluting with DCM:2M MeOH/NH3 (1:0 to 49:1, 22 CV). Product-containing fractions were evaporated to dryness to give a dark yellow solid (134 mg)

1. stirringto stir under nitrogen for 45 minutes
2. waitthe reaction was left
3. stirringto stir under nitrogen for 4.5 days
4. washeluting with MeOH (40 mL)
5. customProduct-containing fractions were evaporated to dryness
6. customto give a yellow solid
7. customThis was partitioned between sodium bicarbonate (20 mL) and EtOAc (100 mL)
8. extractionThe aqueous layer was extracted with EtOAc (70 mL)
9. washwashed (brine (50 mL))
10. dry with materialdried (sodium sulfate)
11. filtrationfiltered
12. customevaporated to dryness

ORD record

ord-71d543832c5246ba8eff162f35be46b0

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697725B2