Potassium Hydroxide → 3-(2-furanylmethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine

HRID 280331Notes

Reaction equation

HRID 280331 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[NH:16][CH:17]1[CH2:22][CH2:21][N:20](C(OCC)=O)[CH2:19][CH2:18]1.[OH-].[K+]>O.CC(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[NH:16][CH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 13587980ethyl 4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridine-2-yl]amino]-1-piperidinecarboxylate

Product 1

HCID 135880653-(2-furanylmethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amineYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 50 parts of ethyl 4-[[3-(2-furanylmethyl)-3H-imidazo-[4,5-b]pyridin-2-yl]amino]-1-piperidinecarboxylate, 50 parts of potassium hydroxide, 400 parts of 2-propanol and 20 drops of water was stirred and refluxed for about 5 hours. The reaction mixture was evaporated and water was added to the residue. The product was extracted twice with 4-methyl-2-pentanone. The combined extracts were dried, filtered and evaporated. The solid residue was stirred in 1,1'-oxybisethane. The product was filtered off and dried, yielding 34 parts (85%) of 3-(2-furanylmethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]-pyridin-2-amine; mp. 159.0° C. (35).

Workup

  1. temperaturerefluxed for about 5 hours
  2. customThe reaction mixture was evaporated
  3. additionwater was added to the residue
  4. extractionThe product was extracted twice with 4-methyl-2-pentanone
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. customevaporated
  8. stirringThe solid residue was stirred in 1,1'-oxybisethane
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-a34e6c9b38b64beab39fe71b23fb0b98
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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