Triethylamine → N-[(4-fluorophenyl)-methyl]-4-methyl-2-propyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[CH3:41][C:42]1[C:51]2[C:46](=[CH:47][C:48]([C:52]([F:55])([F:54])[F:53])=[CH:49][CH:50]=2)[N:45]=[C:44]([CH2:56][CH2:57][CH3:58])[C:43]=1[C:59](O)=[O:60]>C1COCC1.CC(=O)OCC.CCOC(C)=O.CCCCCC>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:59]([C:43]2[C:44]([CH2:56][CH2:57][CH3:58])=[N:45][C:46]3[C:51]([C:42]=2[CH3:41])=[CH:50][CH:49]=[C:48]([C:52]([F:55])([F:54])[F:53])[CH:47]=3)=[O:60])=[CH:4][CH:3]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
311 μl (2.7 mmol) 4-fluorobenzylamine, 941 mg (2.5 mmol) HATU and 1 ml (7.2 mmol) NEt3 were added consecutively to a solution of 740 mg (2.5 mmol) 4-methyl-2-propyl-7-(trifluoromethyl)quinoline-3-carboxylic acid in THF (19 ml) and the mixture was then stirred for 72 h at 50° C. The mixture was then diluted with EA 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. After CC (EtOAc/hexane 1:1) of the residue, 770 mg (1.9 mmol, 76%) N-[(4-fluorophenyl)-methyl]-4-methyl-2-propyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (example 3) was obtained. MS: m/z 405.2 [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-f42e3a17cf1844a4b3f34c85667b1251
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445512B2
Reaction notes
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