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Diisopropylamine → (E)-4,4,5,5,5-Pentafluoro-N-[3-methyl-2-(4-quinolylamino)butyl]pent-2-enamide

HRID 333053
Notes
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Reaction equation

HRID 333053 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 651919333-Methyl-N2-(4-quinolyl)butane-1,2-diamineHCID 86691160(2E)-4,4,5,5,5-Pentafluoro-2-pentenoic acid

Product 1

HCID 56947333
(E)-4,4,5,5,5-Pentafluoro-N-[3-methyl-2-(4-quinolylamino)butyl]pent-2-enamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature for 3 hours
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. customthe resulting residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  5. customto yield 7.3 mg (0.018 mmol, 12%)

Sources & evidence

ORD record
ord-b947f5f9f3644b588defcbc6bafc2af4
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877934B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes