Ethyl 4-[[[[2-[[(5-ethyl-2-furanyl)methyl]amino]-3-pyridinyl]amino]thioxomethyl]amino]-1-piperidinecarboxylate → ethyl 4-[[3-[(5-ethyl-2-furanyl)methyl]-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidinecarboxylate

HRID 330538Notes

Reaction equation

HRID 330538 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([CH2:8][NH:9][C:10]2[C:15]([NH:16][C:17]([NH:19][CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]3)=S)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1)[CH3:2]>[Hg]=O.C(O)C>[CH2:1]([C:3]1[O:7][C:6]([CH2:8][N:9]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[N:16]=[C:17]2[NH:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 14677555Ethyl 4-[[[[2-[[(5-ethyl-2-furanyl)methyl]amino]-3-pyridinyl]amino]thioxomethyl]amino]-1-piperidinecarboxylate

Product 1

HCID 15623999ethyl 4-[[3-[(5-ethyl-2-furanyl)methyl]-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidinecarboxylateYield 83.1%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 50 parts of ethyl 4-[[[[2-[[(5-ethyl-2-furanyl)methyl]amino]-3-pyridinyl]amino]thioxomethyl]amino]-1-piperidinecarboxylate, 32.4 parts of mercury(II) oxide and 480 parts of ethanol was stirred for 1 hour at reflux temperature. The reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated. The residue was stirred in 1,1'-oxybisethane. The crystallized product was filtered off and dried, yielding 38 parts (83.1%) of ethyl 4-[[3-[(5-ethyl-2-furanyl)methyl]-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidinecarboxylate; mp. 111.1° C. (int. 14). In a similar manner there were also prepared:

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered over diatomaceous earth
  3. customthe filtrate was evaporated
  4. stirringThe residue was stirred in 1,1'-oxybisethane
  5. filtrationThe crystallized product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-62c04603fb0b4d18972c66e09bd495de
Source dataset
uspto-grants-1990_01
Patent number
US04897401

Reaction notes

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