Hydrochloric Acid → C-[6-(2,4-Dichloro-phenyl)-8-methoxy-3-morpholin-4-yl-imidazo[1,2-a]pyridin-7yl]-methylamine

A mixture of 8-chloro-6-(2,4-dichloro-phenyl)-3-morpholin-4-yl-imidazo[1,2-a]pyridine-7-carbonitrile (20 mg, 0.05 mmol, prepared according to Example 30, Step 16.1) and NaOMe (8.2 mg, 0.15 mmol) in MeOH (0.5 mL) was refluxed and stirred for 1 h. The reaction mixture was cooled to RT, poured into water (20 ml) and extracted with DCM (3×10 mL). The combined organic fractions were dried over Na2SO4, filtered, and evaporated. The remaining residue was dissolved in THF and a BH3.THF complex (1.0 M solution in THF, 0.2 mL, 0.2 mmol) followed by a 4M HCl solution in dioxane (2 drops) were added. The reaction mixture was stirred and refluxed for 2 h30, then cooled to 0° C. (ice bath) and poured into MeOH. The resulting solution was evaporated to dryness and the remaining residue was purified by reverse phase prep-HPLC (Waters system) to give the title compound (2TFA salt, 3.3 mg, 0.005 mmol, 9% for 2 steps). MS: 407 [M+1]+; HPLC: AtRet=1.09.

1. temperaturewas refluxed
2. extractionextracted with DCM (3×10 mL)
3. dry with materialThe combined organic fractions were dried over Na2SO4
4. filtrationfiltered
5. customevaporated
6. dissolutionThe remaining residue was dissolved in THF
7. additionwere added
8. stirringThe reaction mixture was stirred
9. temperaturerefluxed for 2 h30
10. temperaturecooled to 0° C. (ice bath)
11. customThe resulting solution was evaporated to dryness
12. customthe remaining residue was purified by reverse phase prep-HPLC (Waters system)

ORD record

ord-cf097293f0584f62a1e7f1d2be41f0dd

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097617B2