Triethylamine → (E)-3-Cyclopropyl-N-methyl-N-[2-[methyl-(2-methyl-4-quinolyl)amino]ethyl]prop-2-enamide
Reaction equation
[CH:1]1(/[CH:4]=[CH:5]/[C:6]([OH:8])=O)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:33][N:34]([C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:42]=[C:41]([CH3:49])[CH:40]=1)[CH2:35][CH2:36][NH:37][CH3:38].C(N(CC)CC)C>C1COCC1.CN(C=O)C.C(OCC)(=O)C>[CH:1]1(/[CH:4]=[CH:5]/[C:6]([N:37]([CH3:38])[CH2:36][CH2:35][N:34]([CH3:33])[C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[N:42]=[C:41]([CH3:49])[CH:40]=2)=[O:8])[CH2:2][CH2:3]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
(E)-3-Cyclopropylprop-2-enoic acid (22 mg, 0.2 mmol) and HBTU (76 mg, 0.2 mmol) were dissolved in a 1:1 mixture of anhydrous THF and anhydrous DMF (2 ml). After 5 minutes N,N′-dimethyl-N-(2-methyl-4-quinolyl)ethane-1,2-diamine (52 mg, 0.23 mmol) and triethylamine (62 μl, 0.45 mmol) were added and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution, brine and dried over magnesium sulfate. The solvent was removed under reduced pressure and purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 28.3 mg (0.087 mmol, 43.5%).
Workup
- washwashed with water, saturated sodium bicarbonate solution, brine
- dry with materialdried over magnesium sulfate
- customThe solvent was removed under reduced pressure
- custompurified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
- customto yield 28.3 mg (0.087 mmol, 43.5%)
Sources & evidence
- ORD record
- ord-d7065f1b0f0d4abb86fc86b30d990d13
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877934B2
Reaction notes
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