Pyridine → HCID 67385838, compound

HRID 906010Notes

Reaction equation

HRID 906010 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([NH:12][C:13]2[N:14]=[C:15]3[CH:21]=[CH:20][N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:16]3=[N:17][CH:18]=2)=[O:11])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(Cl)Cl>[C:36]([N:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([NH:12][C:13]2[N:14]=[C:15]3[CH:21]=[CH:20][N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:16]3=[N:17][CH:18]=2)=[O:11])[CH2:5][CH2:4]1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 67385923HCID 67385923, compound

Product 1

HCID 67385838HCID 67385838, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperidin-4-yl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea dihydrochloride (0.073 g, 0.158 mmol) was suspended in DCM (1 mL) and pyridine (0.045 mL, 0.55 mmol) was added. Acetic anhydride (0.018 mL, 0.19 mmol) was added and the resulting solution stirred at RT overnight. The solvent was evaporated. The remaining oil was purified by SiO2 chromatography (12 g SiO2, DCM:MeOH 0 to 5% MeOH) to give 0.053 g of 1-(1-acetyl-piperidin-4-yl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea as off-white foam (78% yield).

Workup

  1. customThe solvent was evaporated
  2. customThe remaining oil was purified by SiO2 chromatography (12 g SiO2, DCM:MeOH 0 to 5% MeOH)

Sources & evidence

ORD record
ord-13a10f83941c4da5976e785f2eca8535
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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