Ethyl 4-amino-1-piperidinecarboxylate → Ethyl 4-[(thiazolo[4,5-c]pyridin-2-yl)amino]-1-piperidinecarboxylate

HRID 1723426Notes

Reaction equation

HRID 1723426 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.CS([C:17]1[S:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N:25]=1)(=O)=O>ClC(Cl)Cl>[S:18]1[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N:25]=[C:17]1[NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 157251382-(Methylsulfonyl)thiazolo[4,5-c]pyridine

Product 1

HCID 14576031Ethyl 4-[(thiazolo[4,5-c]pyridin-2-yl)amino]-1-piperidinecarboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 8.5 parts of ethyl 4-amino-1-piperidinecarboxylate and 2.6 parts of 2-(methylsulfonyl)thiazolo[4,5-c]pyridine was molten together for 1 hour at 120° C. After cooling, the mixture was taken up in trichloromethane. The whole was washed with water and sodium hydroxide, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was stirred in warm 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.8 parts (76%) of ethyl 4-[(thiazolo[4,5-c]pyridin-2-yl)amino]-1-piperidinecarboxylate; mp. 213° C. (66).

Workup

  1. temperatureAfter cooling
  2. washThe whole was washed with water and sodium hydroxide
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-0741c64fcd4d4a8182e8eaa4281e7181
Source dataset
uspto-grants-1989_08
Patent number
US04861785

Reaction notes

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