Ethanol → HCID 131732881, compound

HRID 526445Notes

Reaction equation

HRID 526445 reaction equation
[CH2:1]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][NH2:17])=N[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27](=[CH:33]N(C)C)[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=1)#[N:20].[CH2:37](O)C>C(Cl)Cl>[CH2:1]([NH:8][C:9]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][NH:17][CH:33]=[C:27]([C:24]2[CH:25]=[CH:26][C:21]([C:19]#[N:20])=[CH:22][CH:23]=2)[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:37][CH:11]=1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 51370238N-benzyl-6-hydrazinylpyridine-3-carboxamideHCID 117601544Ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate

Product 1

HCID 131732881HCID 131732881, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combined N-benzyl-6-hydrazinylnicotinamide (126 mg, 0.520 mmol) and ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate (127 mg, 0.520 mmol) in ethanol (10 mL) and stirred at room temperature overnight. The reaction mixture was evaporated to give a residue which was dissolved in DCM (100 ml), extracted with saturated aqueous sodium bicarbonate (50 ml), dried with Na2SO4, and concentrated to a residue which was purified by chromatography (12 g SiO2, DCM-MeOH 0 to 10%) to give the title compound (90 mg, 39%) as an oil. MS m/z [M+H]+ 442.4.

Workup

  1. customThe reaction mixture was evaporated
  2. customto give a residue which
  3. extractionextracted with saturated aqueous sodium bicarbonate (50 ml)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated to a residue which
  6. customwas purified by chromatography (12 g SiO2, DCM-MeOH 0 to 10%)

Sources & evidence

ORD record
ord-e84993cc66074fd2b5de187ba02460bf
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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