Diisopropyl Ether → HCID 20060696, compound

HRID 1085675Notes

Reaction equation

HRID 1085675 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1)=[C:2]=[S:3].[Cl:15][C:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=1.O(C(C)C)C(C)C>C(O)C>[ClH:15].[N:22]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[S:3][C:2]=1[NH:1][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 805282-Chloro-3-pyridylamineHCID 3018454Ethyl 4-isothiocyanatopiperidine-1-carboxylate

Product 1

HCID 20060696HCID 20060696, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 51 parts of ethyl 4-isothiocyanato-1-piperidinecarboxylate, 30 parts of 2-chloro-3-pyridinamine and 240 parts of ethanol was stirred and refluxed for 24 hours. The reaction mixture was cooled to room temperature. Upon the addition of 70 parts of 2,2'-oxybispropane, the product was allowed to crystallize. It was filtered off and dried, yielding 40 parts (50%) of ethyl 4-(thiazolo[5,4-b]pyridin-2-ylamino)-1-piperidinecarboxylate monohydrochloride (65).

Workup

  1. temperaturerefluxed for 24 hours
  2. customto crystallize
  3. filtrationIt was filtered off
  4. customdried

Sources & evidence

ORD record
ord-389ec53291294fae8c8ffc672ce2e683
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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