Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (E)-4,4,5,5,5-Pentafluoro-N-[2-[[2-(2-methyl-1,3-dioxolan-2-yl)-4-pyridyl]amino]-ethyl]pent-2-enamide

HRID 333063Notes

Reaction equation

HRID 333063 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.[CH3:37][C:38]1([C:43]2[CH:48]=[C:47]([NH:49][CH2:50][CH2:51][NH2:52])[CH:46]=[CH:45][N:44]=2)[O:42][CH2:41][CH2:40][O:39]1>CN(C=O)C.C1COCC1.C(OCC)(=O)C>[F:12][C:2]([F:1])([C:8]([F:11])([F:10])[F:9])/[CH:3]=[CH:4]/[C:5]([NH:52][CH2:51][CH2:50][NH:49][C:47]1[CH:46]=[CH:45][N:44]=[C:43]([C:38]2([CH3:37])[O:42][CH2:41][CH2:40][O:39]2)[CH:48]=1)=[O:7]

Participants

7

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66835538N-[2-(2-Methyl-1,3-dioxolan-2-yl)-4-pyridyl]ethane-1,2-diamineHCID 86691160(2E)-4,4,5,5,5-Pentafluoro-2-pentenoic acid

Product 1

HCID 56949209(E)-4,4,5,5,5-Pentafluoro-N-[2-[[2-(2-methyl-1,3-dioxolan-2-yl)-4-pyridyl]amino]-ethyl]pent-2-enamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-4,4,5,5,5-Pentafluoropent-2-enoic acid (133 mg, 0.7 mmol) and HBTU (265 mg, 0.7 mmol) were dissolved in a 2:1 mixture of anhydrous DMF and anhydrous THF (3 ml) and stirred at room temperature for 15 minutes. N-[2-(2-Methyl-1,3-dioxolan-2-yl)-4-pyridyl]ethane-1,2-diamine (100 mg, 0.45 mmol) was added and stirring was continued for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 47 mg (0.12 mmol, 26%).

Workup

  1. stirringstirring
  2. waitwas continued for 3 hours
  3. washwashed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated 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 47 mg (0.12 mmol, 26%)

Sources & evidence

ORD record
ord-44f018768c4f46e1a43498f7569c161a
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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