Triethylamine → (E)-4,4,5,5,5-Pentafluoro-N-[3-[(2-methyl-4-quinolyl)amino]propyl]pent-2-enamide

HRID 333065Notes

Reaction equation

HRID 333065 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(N(CC)CC)C.Cl.[CH3:45][C:46]1[CH:55]=[C:54]([NH:56][CH2:57][CH2:58][CH2:59][NH2:60])[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3]>CN(C=O)C.C(#N)C>[F:12][C:2]([F:1])([C:8]([F:11])([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([NH:60][CH2:59][CH2:58][CH2:57][NH:56][C:54]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]=[C:46]([CH3:45])[CH:55]=1)=[O:7]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 17999421N1-(2-Methylquinolin-4-YL)propane-1,3-diamine hydrochlorideHCID 86691160(2E)-4,4,5,5,5-Pentafluoro-2-pentenoic acid

Product 1

HCID 86691162(E)-4,4,5,5,5-Pentafluoro-N-[3-[(2-methyl-4-quinolyl)amino]propyl]pent-2-enamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

(E)-4,4,5,5,5-Pentafluoropent-2-enoic acid (38 mg, 0.2 mmol) and HBTU (76 mg, 0.2 mmol) were dissolved in a 1:1 mixture of anhydrous DMF and anhydrous acetonitrile (2 ml), after 5 minutes triethylamine (82 μl, 0.6 mmol) and N-(2-methyl-4-quinolyl)propane-1,3-diamine hydrochloride (48 mg, 0.24 mmol) was added and stirring was continued for 3 hours. To the mixture basic aluminium oxide was added, stirring was continued for one hour, the mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 28.4 mg (0.076 mmol, 38%).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for one hour
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated to dryness under reduced pressure
  6. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  7. customto yield 28.4 mg (0.076 mmol, 38%)

Sources & evidence

ORD record
ord-0d5bac1625eb4331b0eff6a63b8e83d3
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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