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

HRID 1762815Notes

Reaction equation

HRID 1762815 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[N:21]=[C:20]1[NH2:28].CC1C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>O.C(O)(=O)C.C(O)C.CC1C=CC=CC=1>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[N:21]=[C:20]1[NH:28][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

9

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 4311764Sodium borohydrideHCID 156239903-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-amine

Product 1

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

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 22.2 parts of ethyl 4-oxo-1-piperidinecarboxylate, 21.4 parts of 3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-amine, 360 parts of methylbenzene and 0.1 parts of 4-methylbenzenesulfonic acid was stirred for 4 days at reflux temperature using a water separator. After cooling to 50° C., 64 parts of ethanol were added and 3.8 parts of sodium tetrahydroborate were added portionwise to the reaction mixture. Upon completion, stirring was continued for 2 hours at 50° C. After cooling, the mixture was decomposed with 3.5 parts of acetic acid. Water was added to the mixture while stirring and the layers were separated. The aqueous layer was extracted with methylbenzene. The combined methylbenzene layers were dried, filtered and evaporated, yielded ethyl 4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidinecarboxylate as an oily residue (compound 56).

Workup

  1. temperatureat reflux temperature
  2. stirringUpon completion, stirring
  3. waitwas continued for 2 hours at 50° C
  4. temperatureAfter cooling
  5. stirringwhile stirring
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with methylbenzene
  8. dry with materialThe combined methylbenzene layers were dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-cb22403b665242be9a49f9d80e93a144
Source dataset
uspto-grants-1989_05
Patent number
US04835161

Reaction notes

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