Triethylamine → HCID 178478259, compound

HRID 2359030Notes

Reaction equation

HRID 2359030 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:13]1C=CN=CN=1)[C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[Cl:12])=O.O.[NH2:21]N.C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C>C(O)C>[Cl:12][C:11]1[CH:10]=[CH:9][S:8][C:7]=1[C:5]1[C:4]([C:13]2[CH:27]=[CH:26][N:25]=[CH:28][CH:29]=2)=[CH:3][NH:2][N:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 67260928HCID 67260928, compound

Product 1

HCID 178478259HCID 178478259, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(dimethylamino)-1-(3-chloro-2-thienyl)-2-(pyrimidin-4-yl)prop-2-en-1-one (1 eq, 20 mmol) in ethanol (60 mL) was added hydrazine hydrate (1.5 eq, 30 mmol) and triethylamine (1.5 eq, 30 mmol). The reaction mixture was stirred at reflux for 2 h. The mixture was evaporated under reduced pressure. The obtained residue was dissolved in dichloromethane (100 mL) and methanol (10 mL), washed with brine (3×50 mL), dried over Na2SO4 and concentrated. The crude product was suspended in ethylacetate, filtered and dried to afford 2.9 g of 4-(3-(3-chloro-2-thienyl)-1H-pyrazol-4-yl)pyridine (55% yield).

Workup

  1. temperatureat reflux for 2 h
  2. customThe mixture was evaporated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in dichloromethane (100 mL)
  4. washmethanol (10 mL), washed with brine (3×50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-b236bab8bc154770936618647cf54885
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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