Diisopropylamine → (E)-4,4,5,5,5-Pentafluoro-N-[3-methyl-2-(4-quinolylamino)butyl]pent-2-enamide
Reaction equation
[F:1][C:2]([F:12])([C:8]([F:11])([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C.[CH3:44][CH:45]([CH3:60])[CH:46]([NH:49][C:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[N:53]=[CH:52][CH:51]=1)[CH2:47][NH2:48].C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:12][C:2]([F:1])([C:8]([F:11])([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([NH:48][CH2:47][CH:46]([NH:49][C:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[N:53]=[CH:52][CH:51]=1)[CH:45]([CH3:60])[CH3:44])=[O:7]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
(E)-4,4,5,5,5-Pentafluoropent-2-enoic acid (29 mg, 0.15 mmol) was dissolved in anhydrous DMF (1 ml), HBTU (60 mg, 0.15 mmol) and diisopropylamine (26 μl, 0.15 mmol) were added and the mixture was stirred at room temperature for 15 minutes. 3-Methyl-N2-(4-quinolyl)butane-1,2-diamine (34.4 mg, 0.15 mmol) dissolved in 1 ml anhydrous DMF together with diisopropylethylamine (26 μl, 0.15 mmol) was added and the resulting mixture was stirred at room temperature for 3 hours. The mixture was evaporated to dryness under reduced pressure and the resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 7.3 mg (0.018 mmol, 12%).
Workup
- additionwas added
- stirringthe resulting mixture was stirred at room temperature for 3 hours
- customThe mixture was evaporated to dryness under reduced pressure
- customthe resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
- customto yield 7.3 mg (0.018 mmol, 12%)
Sources & evidence
- ORD record
- ord-b947f5f9f3644b588defcbc6bafc2af4
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877934B2
Reaction notes
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