Lithium Chloride → HCID 70115228, compound

HRID 1018815Notes

Reaction equation

HRID 1018815 reaction equation
[CH:1]1([CH2:7][CH2:8][NH:9][CH2:10][C:11]#[CH:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)S(O[C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:30][CH2:29][C:28]([CH3:32])([CH3:31])[CH2:27][CH2:26]2)=[CH:21][C:20]=1[Cl:33])(=O)=O.[Cl-].[Li+]>C(N(CC)CC)C.N1C=CC=CC=1.C(OCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[ClH:33].[CH3:31][C:28]1([CH3:32])[CH2:29][CH2:30][CH:25]([C:22]2[CH:23]=[CH:24][C:19]([C:12]#[C:11][CH2:10][NH:9][CH2:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:20]([Cl:33])[CH:21]=2)[CH2:26][CH2:27]1

Participants

9

Reactant 3

HCID 433294Lithium ChlorideHCID 22390454HCID 22390454, compound2×HCID 62142207HCID 62142207, compound2×

Product 1

HCID 70115228HCID 70115228, compound

Reagents, catalysts & solvents 5

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

1.42 g of dichlorobis(triphenylphosphine)palladium are added, under an inert atmosphere, to 8.03 g of cyclohexylethylprop-2-ynylamine (compound 4.1), 15 g of [4-(4,4-dimethylcyclohexyl)-2-chlorophenyl] trifluoromethanesulphonate (compound 111.1), 0.19 g of copper iodide, 3.4 g of lithium chloride in 200 ml of triethylamine and 100 ml of pyridine. The reaction mixture is refluxed for 12 hours. The solvents are evaporated off under reduced pressure and the residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/ethyl acetate mixture varying from 95/5 to 90/10 (v/v). The residue obtained is taken up in diethyl ether. The hydrochloride is separated out by filtration and hydrogen chloride is then bubbled through. The residue obtained is recrystallized from ethyl acetate.

Workup

  1. temperatureThe reaction mixture is refluxed for 12 hours
  2. customThe solvents are evaporated off under reduced pressure
  3. customthe residue obtained
  4. customis purified by chromatography on a column of silica gel
  5. washeluting with a cyclohexane/ethyl acetate mixture
  6. customThe residue obtained
  7. customThe hydrochloride is separated out by filtration and hydrogen chloride
  8. customis then bubbled through
  9. customThe residue obtained
  10. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1e8fad360e584ecfa72ef68542cfaae6
Source dataset
uspto-grants-2002_11
Patent number
US06482986B1

Reaction notes

Loading…