Pyridine → 1-(1-propionyl-piperidin-3-yl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

HRID 906011Notes

Reaction equation

HRID 906011 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:2]1.N1C=CC=CC=1.[C:34](Cl)(=[O:37])[CH2:35][CH3:36]>C(Cl)Cl>[C:34]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:2]1)(=[O:37])[CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 67385591Piperidin-3-yl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

Product 1

HCID 673862241-(1-propionyl-piperidin-3-yl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ureaYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Piperidin-3-yl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.150 g, 0.38 mmol) was dissolved in 2 mL of DCM and pyridine was added (0.120 mL/1.54 mmol). Propionyl chloride (0.05 mL, 5.4 mmol) was added dropwise to the solution and the resulting mixture was stirred overnight at RT. The reaction mixture was diluted with DCM and was quenched by addition of saturated solution of NaHCO3. The aqueous layer was extracted once with DCM and the combined organics were dried (MgSO4), filtered and, concentrated. The crude was purified by SiO2 chromatography using DCM/(DCM:MeOH:NH4OH; 60:10:1) 75% DCM) to give 0.130 g of 1-(1-propionyl-piperidin-3-yl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (76% yield).

Workup

  1. customwas quenched by addition of saturated solution of NaHCO3
  2. extractionThe aqueous layer was extracted once with DCM
  3. dry with materialthe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-28df21a71ef84f9e8c28152e29d94deb
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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