Isopropanol → HCID 19707185, compound

HRID 726582Notes

Reaction equation

HRID 726582 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.CN([CH:22]=[N:23][NH:24][C:25](OCC)=[O:26])C.CC(O)C>S1CCCC1>[O:26]=[C:25]1[N:1]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]3)=[N:6][CH:7]=2)[CH:22]=[N:23][NH:24]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 19707182HCID 19707182, compoundHCID 54558834HCID 54558834, compound

Product 1

HCID 19707185HCID 19707185, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 1127TetrahydrothiopheneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 4-(5-amino-2-pyridinyl)-1-piperazinecarboxylate (0.18 mol) and ethyl 2-[(dimethylamino)methylene]hydrazinecarboxylate (0.54 mol) in tetrahydrothiophene, 1,1-dioxide (50 ml) was stirred at 150° C. for 3 hours. The mixture was cooled till 100° C., 2-propanol was added until crystallization. The precipitate was filtered and recrystallized from methanol; yielding 30.5 g ethyl 4-[5-(2,3-dihydro-3-oxo-4H-1,2,4-triazol-4-yl)-2-pyridinyl]-1-piperazinecarboxylate (53.3%); mp. 220.8° C. (interm. 1).

Workup

  1. temperatureThe mixture was cooled till 100° C.
  2. filtrationThe precipitate was filtered
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-edf7113356cb452ab444adee9017ad15
Source dataset
uspto-grants-1998_01
Patent number
US05710156

Reaction notes

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