N,N-Dimethylethylenediamine → 5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-N-[2-(dimethylamino)ethyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

HRID 2089251Notes

Reaction equation

HRID 2089251 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[C:16]([C:32](OCC)=[O:33])[C:17](=[O:31])[N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[C:19]=3[CH3:20])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].[CH3:37][N:38]([CH3:42])[CH2:39][CH2:40][NH2:41]>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[C:16]([C:32]([NH:41][CH2:40][CH2:39][N:38]([CH3:42])[CH3:37])=[O:33])[C:17](=[O:31])[N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=4)[C:19]=3[CH3:20])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 58218050Ethyl 5-[2-(4-cyanophenyl)-2H-pyrazole-3-yl]-6-methyl-2-oxo-1-(3-trifluoromethylphenyl)-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 670929825-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-N-[2-(dimethylamino)ethyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideYield 67%

Procedure

Intermediate A and N,N-dimethylethane-1,2-diamine were reacted together using an analogous method to that described in Step 1 of Example 1 to afford 5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-N-[2-(dimethylamino)ethyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (154 mg, 67%); 1H NMR (500 MHz, DMSO) δ 1.72 (3H, s), 2.10 (6H, s), 2.32 (2H, t), 3.36-3.32 (2H, m), 6.72 (1H, d), 7.67-7.64 (2H, m), 7.71 (1H, d), 7.88-7.82 (2H, m), 7.96-7.90 (4H, m), 8.07 (1H, s), 9.37 (1H, t); APCI-MSm/z: 535[MH+H]

Sources & evidence

ORD record
ord-a1cc33f6eb7e42f79e563edb9fe33225
Source dataset
uspto-grants-2013_05
Patent number
US08436024B2

Reaction notes

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