Dimethyl Sulfoxide → HCID 67241715, compound

Temperature

150 °C

Combined 2,4-dichlorothiazole (405 mg, 2.63 mmol), 3-oxo-1,4-diazepan-1-ium trifluoroacetate (preparation described in Intermediate XX, 600 mg, 2.63 mmol), potassium phosphate tribasic (1395 mg, 6.57 mmol) and DMSO (22.00 ml) in a round bottomed flask, fitted with water-cooled condenser, balloon and septum. The mixture was heated to 150° C. for 7 hours with stirring. The dark solution was diluted with 100 mL 10% IPA/CHCl3, 40 mL water, mL aq. NaHCO3(sat.). The resulting suspension was extracted with 10% IPA/CHCl3, and the organic layers were combined and washed successively with water and brine. The organic fractions were pooled and concentrated to dryness. The residue was then loaded directly onto silica gel and purified by preparative HPLC Normal phase, eluting with CH2Cl2/MeOH (0-30%). The 3rd peak was collected and concentrated to afford 4-(4-chloro-1,3-thiazol-2-yl)-1,4-diazepan-2-one (179 mg, 0.773 mmol, 29.4% yield) as a brown solid.

1. temperaturecooled condenser
2. extractionThe resulting suspension was extracted with 10% IPA/CHCl3
3. washwashed successively with water and brine
4. concentrationconcentrated to dryness
5. custompurified by preparative HPLC Normal phase
6. washeluting with CH2Cl2/MeOH (0-30%)
7. customThe 3rd peak was collected
8. concentrationconcentrated

ORD record

ord-ec39d4321e0949da86e46349511d7ad5

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735417B2