Triethylamine → N'-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridazin-3-yl)-2-methoxyacetohydrazide

HRID 1661101Notes

Reaction equation

HRID 1661101 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([NH:14][NH2:15])=[N:12][N:11]([CH2:16][C:17]3[C:18]([CH3:27])=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=3)[C:10](=[O:28])[C:9]=2[C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:44][O:45][CH2:46][C:47](Cl)=[O:48]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([NH:14][NH:15][C:47](=[O:48])[CH2:46][O:45][CH3:44])=[N:12][N:11]([CH2:16][C:17]3[C:18]([CH3:27])=[N:19][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:22]=3)[C:10](=[O:28])[C:9]=2[C:29]2[CH:30]=[CH:31][C:32]([C:33]#[N:34])=[CH:35][CH:36]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 671287294-(5-(4-Chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile

Product 1

HCID 67128631N'-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridazin-3-yl)-2-methoxyacetohydrazideYield 57.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5-(4-chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile (1200 mg, 2.344 mmol) in THF (15 ml) was added Et3N (471 mg, 4.668 mmol) followed by 2-methoxyacetyl chloride (254 mg, 2.344 mmol). The reaction was stirred at room temperature for 20 min. After this time, the reaction was diluted with EtOAc (100 ml) and the resulting solution was wash with water (2×50 ml) and saturated NaCl (50 ml). The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified using an ISCO automated chromatography system (120 g silica gel, 20-60% EtOAc/CH2Cl2) to the give product N′-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridazin-3-yl)-2-methoxyacetohydrazide as a light yellow solid 780 mg (57% yield). HPLC retention time 2.858 min (Method A); LCMS (M+H)=583.0.

Workup

  1. washthe resulting solution was wash with water (2×50 ml) and saturated NaCl (50 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-f9ebdbd334844c70b587abc91449d0d1
Source dataset
uspto-grants-2011_10
Patent number
US08030306B2

Reaction notes

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