Reaction #57240

Reaction equation

1,1-dimethylethyl 4-[4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate

hydrochloric acid

4-morpholine carbonyl chloride

→

title compound

Yield 55.0%

4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-2-[1-(4-morpholinylcarbonyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Yield 55.0%

Solvents

dioxane

Conditions

Workup

1. 1
   ConcentrationThe reaction was concentrated in vacuo
2. 2
   Otherevaporated one time from methylene chloride
3. 3
   workup.STIRRINGstirred 48 h
4. 4
   ConcentrationThe reaction was concentrated
5. 5
   Otherpurification of the residue by Gilson reverse phase HPLC

Procedure

A solution of 1,1-dimethylethyl 4-[4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate (0.38 mmol) methylene chloride (1 mL) was treated with 4N hydrochloric acid in dioxane (1 mL) and stirred for 1 h at room temperature. The reaction was concentrated in vacuo and evaporated one time from methylene chloride. The resultant residue was suspended in pyridine (5 mL) and treated with 4-morpholine carbonyl chloride (3.00 mmol) and stirred 48 h. The reaction was concentrated and purification of the residue by Gilson reverse phase HPLC provided the title compound (55%). ESMS [M+H]+: 668.4

Source