Trifluoroacetic acid → HCID 131732882, compound

HRID 578947

Reaction equation

HRID 578947 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.CN(C)[CH:21]=[C:22]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[C:23]([O:25][CH3:26])=[O:24].[C:34](O)(C(F)(F)F)=O>C(O)C.CCOC(C)=O>[CH2:1]([NH:8][C:9]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][NH:17][CH:21]=[C:22]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[C:23]([O:25][CH3:26])=[O:24])=[CH:34][CH:11]=1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 51370238N-benzyl-6-hydrazinylpyridine-3-carboxamideHCID 73047442Methyl 3-(dimethylamino)-2-(2-pyridinyl)-2-propenoate

Product 1

HCID 131732882HCID 131732882, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combined N-benzyl-6-hydrazinylnicotinamide (200 mg, 0.826 mmol), methyl 3-(dimethylamino)-2-(pyridin-2-yl)acrylate (170 mg, 0.826 mmol) and TFA (0.127 mL, 1.651 mmol) in ethanol (3 mL) and stirred overnight at room temperature. The reaction mixture was diluted in EtOAc (50 mL), washed with saturated aqueous sodium bicarbonate (20 ml), brine (20 ml), dried with Na2SO4 and concentrated to give the title compound (244 mg) as an orange solid, was used without further purification. MS m/z [M+H]+ 404.4.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (20 ml), brine (20 ml)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cbf05fdc8c4644d99ee17a5792b8df75
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Linked notes

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