Hydrochloric Acid → HCID 178428089, compound

HRID 578940Notes

Reaction equation

HRID 578940 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[CH:25]N(C)C)[C:20](OCC)=[O:21])=[CH:15][CH:14]=1)#[N:12].Cl.CCN(C(C)C)C(C)C>C(O)(C)C>[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([N:8]2[C:20]([OH:21])=[C:19]([C:16]3[CH:15]=[CH:14][C:13]([C:11]#[N:12])=[CH:18][CH:17]=3)[CH:25]=[N:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 534029851-(5-Bromo-4-methylpyridin-2-YL)hydrazineHCID 117601544Ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate

Product 1

HCID 178428089HCID 178428089, compoundYield 82.04%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combined 5-bromo-2-hydrazinyl-4-methylpyridine (6.0 g, 29.85 mmol) and isopropanol (100 mL) and added ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate (8.02 g, 32.84 mmol) and HCl solution (aqueous, 1.85%, 49.75 mL) and stirred at room temperature for 2 h, then DIEA (19.40 g, 149.25 mmol) was added. After about 30 minutes the reaction was evaporated to give a residue which was extracted with EtOAc (50 mL×2) and water (50 mL×2), the EtOAc layers were combined and washed with brine, dried over Na2SO4 to give a residue which was purified by flash chromatography (petroleum ether:EtOAc 5:1-1:8) to give the title compound (8.67 g, 82.04%).

Workup

  1. customAfter about 30 minutes the reaction was evaporated
  2. customto give a residue which
  3. extractionwas extracted with EtOAc (50 mL×2) and water (50 mL×2)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customto give a residue which
  7. customwas purified by flash chromatography (petroleum ether:EtOAc 5:1-1:8)

Sources & evidence

ORD record
ord-113e1756e23244cc9384392f88075bc5
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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