Triethylamine → 2-ethoxy-4-methyl-N-(thiophene-2-yl-methyl)-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH2:7].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[CH2:39]([O:41][C:42]1[C:51]([C:52](O)=[O:53])=[C:50]([CH3:55])[C:49]2[C:44](=[CH:45][C:46]([C:56]([F:59])([F:58])[F:57])=[CH:47][CH:48]=2)[N:43]=1)[CH3:40]>C1COCC1.CCOC(C)=O>[CH2:39]([O:41][C:42]1[C:51]([C:52]([NH:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:53])=[C:50]([CH3:55])[C:49]2[C:44](=[CH:45][C:46]([C:56]([F:59])([F:57])[F:58])=[CH:47][CH:48]=2)[N:43]=1)[CH3:40]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
53 μl (0.5 mmol) thiophene methane amine, 172 mg (0.5 mmol) HATU and 165 μl (1.2 mmol) NEt3 were added consecutively to a solution of 123 mg (0.4 mmol) 2-ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid in THF (3 ml) and thereafter stirred for 16 h at RT. The solution was subsequently diluted with EtOAc and washed with a 4N aq. NH4CL sol., a 1M aq. Na2CO3 sol. and brine. The organic phase was dried over MgSO4, filtered through silica gel and concentrated in a vacuum. 116 mg (0.3 mmol, 72%) 2-ethoxy-4-methyl-N-(thiophene-2-yl-methyl)-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (example 2) was obtained as a residue. MS: m/z 395.1 [M+H]+.
Workup
- washwashed with a 4N aq. NH4CL sol.
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered through silica gel
- concentrationconcentrated in a vacuum
Sources & evidence
- ORD record
- ord-7bbcbee1f85b42939bbeaafaa08d93d9
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073862B2
Reaction notes
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