Triethylamine → (E)-N-[2-[(2-Methyl-4-quinolyl)amino]ethyl]but-2-enamide
Reaction equation
C[CH:2](C)/[CH:3]=[CH:4]/[C:5](O)=[O:6].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:33][C:34]1[CH:43]=[C:42]([NH:44][CH2:45][CH2:46][NH2:47])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=1.C(N(CC)CC)C>C(#N)C>[CH3:33][C:34]1[CH:43]=[C:42]([NH:44][CH2:45][CH2:46][NH:47][C:5](=[O:6])/[CH:4]=[CH:3]/[CH3:2])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(E)-4-Methylpent-2-enoic acid (190 mg, 1.3 mmol) was mixed together with HBTU (470 mg, 1.3 mmol) and N-(2-methyl-4-quinolyl)ethane-1,2-diamine (250 mg, 1.2 mmol) in acetonitrile (5 ml). Triethylamine (1 mll) was added with stirring at 0° C. over 15 minutes and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure, the residue was dissolved in DCM and washed with a saturated solution of sodium bicarbonate. The combined aqueous solutions were extracted three times with DCM. The organic layers were combined, dried over sodium sulfate, the solvent was removed under reduced pressure to give 245 mg of a yellow solid (0.82 mmol, 66%). MS (APCI) m/z=298.2 [M+1]+.
Workup
- stirringthe resulting mixture was stirred at room temperature overnight
- customThe volatiles were removed under reduced pressure
- dissolutionthe residue was dissolved in DCM
- washwashed with a saturated solution of sodium bicarbonate
- extractionThe combined aqueous solutions were extracted three times with DCM
- dry with materialdried over sodium sulfate
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-5f64f7331f114d09a892ddee5f9bd4b8
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877934B2
Reaction notes
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