Acetone → 3-(isopropylamino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one

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Reaction Steps

3-Amino-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)propan-1-one (0.040 g, 0.095 mmol, see Example 21) and acetone (0.0696 mL, 0.947 mmol) were placed in 1:1 dichloroethylene (“DCE”):DMF (2 mL). DIEA (d 0.742; 0.0495 mL, 0.284 mmol) was then added, followed by the addition of NaBH(OAc)3 (0.0401 g, 0.189 mmol). The reaction was then stirred for 30 minutes. The reaction was then poured into aqueous Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, and concentrated to give a crude residue. The residue was purified by chromatography (9:1 DCM:MeOH) to give the pure product. The solid was then dissolved in minimal MeOH, and then 1M HCL in ether was added. The precipitate was collected, washed with ether and dried to give 3-(isopropylamino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one (0.005 g, 11.4% yield) as the dihydrochloride salt. MS ESI (+) m/z 392 detected.

Provenance & Evidence