Piperidinium acetate → HCID 57893425, compound

HRID 2046249Notes

Reaction equation

HRID 2046249 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][NH:5][C:4](=[O:14])[C:3]=1[C:15]([O:17]CC)=O.[C:20]([O-:23])(=[O:22])[CH3:21].[NH2+:24]1CCCCC1.C(O)C.C1(C)C=CC=CC=1.N12CCCC=C1CCCCN2>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][NH:5][C:4](=[O:14])[C:3]=1[C:15]([NH:24][CH2:21][C:20]([OH:23])=[O:22])=[O:17]

Participants

6

Reactant 4

HCID 3014295Piperidinium acetateHCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 21863594Toluene ethanolHCID 68812286HCID 68812286, compound

Product 1

HCID 57893425HCID 57893425, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 5-hydroxy-3-oxo-6-phenyl-2,3-dihydro-4-pyridazinecarboxylate. A 1 M solution of piperidinium acetate in 5% ethanol/toluene (1.10 mL, 1.10 mmol) was added to a solution of the compound from example 4(a) (0.350 g, 1.14 mmol) in toluene (10 mL) and the mixture stirred under reflux for 1 h. Diazabicyclo[5.4.0]undec-7-ene (0.30 mL, 2.00 mmol) was added and the reflux continued for 2 h. After cooling, the mixture was partitioned between 1M aqueous hydrochloric acid and ethyl acetate. The extracts were dried (MgSO4), evaporated under reduced pressure and the residue chromatographed (silica gel, 2-8% methanol/dichloromethane). The partially purified product was triturated with ether to give the title compound (0.115 g, 39%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (t, J=7.20 Hz, 3H) 4.32 (q, J=7.16 Hz, 2H) 7.43-7.49 (m, 3H) 7.64-7.67 (m, 2H) 13.05 (s, 1H).

Workup

  1. temperatureunder reflux for 1 h
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between 1M aqueous hydrochloric acid and ethyl acetate
  4. dry with materialThe extracts were dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customthe residue chromatographed (silica gel, 2-8% methanol/dichloromethane)
  7. customThe partially purified product was triturated with ether

Sources & evidence

ORD record
ord-2fe5bcb60798440da87f46278af31cb5
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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