Potassium Hydroxide → HCID 15624012, compound

HRID 330540Notes

Reaction equation

HRID 330540 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[N:10]=[C:9]2[NH:17][CH:18]2[CH2:23][CH2:22][N:21](C(OCC)=O)[CH2:20][CH2:19]2)=[CH:4][CH:3]=1.[OH-].[K+]>CC(O)C>[CH3:1][C:2]1[O:6][C:5]([CH2:7][N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[N:10]=[C:9]2[NH:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15624011HCID 15624011, compound

Product 1

HCID 15624012HCID 15624012, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 20.5 parts of ethyl 4-[[1-[(5-methyl-2-furanyl)methyl]-1H-imidazo[4,5-c]pyridin-2-yl]amino]-1-piperidinecarboxylate, 40 parts of potassium hydroxide and 240 parts of 2-propanol was stirred overnight at reflux temperature. After evaporation, the residue was taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 2-propanone. The product was filtered off and dried, yielding 15 parts (88%) of 1-[(5-methyl-2-furanyl)methyl]-N-(4-piperidinyl)-1H-imidazo[4,5-c]pyridin-2-amine; mp. 185.6° C. (int. 25).

Workup

  1. temperatureat reflux temperature
  2. customAfter evaporation
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from 2-propanone
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-18adc4b738a840d8967bdca36696ded8
Source dataset
uspto-grants-1990_01
Patent number
US04897401

Reaction notes

Loading…