Diisopropylethylamine → (E)-1-[4-(2-Methoxy-4-quinolyl)piperazin-1-yl]-4-methyl-hept-2-en-1-one

HRID 333928

Reaction equation

HRID 333928 reaction equation
[CH3:1][CH:2]([CH2:8][CH2:9][CH3:10])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:44][O:45][C:46]1[CH:55]=[C:54]([N:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]=1>CN(C=O)C>[CH3:44][O:45][C:46]1[CH:55]=[C:54]([N:56]2[CH2:61][CH2:60][N:59]([C:5](=[O:6])/[CH:4]=[CH:3]/[CH:2]([CH3:1])[CH2:8][CH2:9][CH3:10])[CH2:58][CH2:57]2)[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 217202034-Methylhept-2-enoic acidHCID 668358742-Methoxy-4-piperazin-1-yl-quinoline

Product 1

HCID 56948961(E)-1-[4-(2-Methoxy-4-quinolyl)piperazin-1-yl]-4-methyl-hept-2-en-1-oneYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-4-Methyl-hept-2-enoic acid (21.3 mg, 0.15 mmol) was dissolved in DMF (350 μl), diisopropylethylamine was added (26 μl, 0.15 mmol) followed by HATU (57 mg, 0.15 mmol dissolved in 0.25 ml DMF). The mixture was stirred at room temperature for 15 minutes, then 2-methoxy-4-piperazin-1-yl-quinoline (36.4 mg, 0.15 mmol, dissolved in 1 ml DMF) was added and stirring was continued overnight. The mixture was evaporated under reduced pressure, the residue was dissolved in dichloromethane and the resulting solution was washed with 5% sodium bicarbonate solution, water, evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 21.1 mg (0.06 mmol, 39.8%) of a solid.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe mixture was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washthe resulting solution was washed with 5% sodium bicarbonate solution, water
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record
ord-32aec6e0d04d40cf81c859d5b8092f64
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Linked notes

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