Sulfur → ethyl 4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridine-2-yl]amino]-1-piperidinecarboxylate

HRID 1493900Notes

Reaction equation

HRID 1493900 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[C:13]([NH:14][C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]2)=S)=[CH:12][CH:11]=[CH:10][N:9]=1.[S]>[Hg]=O.C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:13]2[N:14]=[C:15]1[NH:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 5362487SulfurHCID 13587973Ethyl 4-[[[2-[(2-furanylmethyl)amino]-3-pyridinyl]aminothioxomethyl]amino]-1-piperidinecarboxylate

Product 1

HCID 13587980ethyl 4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridine-2-yl]amino]-1-piperidinecarboxylateYield 79%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 74 parts of ethyl 4-[[[2-[(2-furanylmethyl)amino]-3-pyridinyl]aminothioxomethyl]amino]-1-piperidinecarboxylate, 96 parts of mercury(II)oxide, 0.1 parts of sulfur and 800 parts of ethanol was stirred and refluxed for 3 hours. The reaction mixture was filtered over Hyflo and the filtrate was evaporated. The residue was crystallized from acetonitrile, yielding 52.5 parts (79%) of ethyl 4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidinecarboxylate; mp. 149.2° C. (intermediate 44).

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe reaction mixture was filtered over Hyflo
  3. customthe filtrate was evaporated
  4. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-1afb4b05fdb04ef580f0b61173656468
Source dataset
uspto-grants-1991_06
Patent number
US05025014

Reaction notes

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