Propargyl alcohol → HCID 10271274, compound

HRID 1070622Notes

Reaction equation

HRID 1070622 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[CH:20]=[C:19](I)[CH:18]=[N:17][C:13]=3[N:14]([CH3:16])[N:15]=2)=[O:9])=[CH:4][CH:3]=1.C(NCC)C.[CH2:30]([OH:33])[C:31]#[CH:32]>CCOC(C)=O.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>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[CH:20]=[C:19]([C:32]#[C:31][CH2:30][OH:33])[CH:18]=[N:17][C:13]=3[N:14]([CH3:16])[N:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 22397218HCID 22397218, compound

Product 1

HCID 10271274HCID 10271274, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, a mixture of N-(4-chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxamide (Preparation 23, 0.053 g), dichlorobis(triphenylphosphine)palladium (II) (4.1 mg), copper(I) iodide (18.3 mg), and diethylamine (1.5 mL) is treated with a solution of propargyl alcohol (11 μL). The reaction mixture is stirred at room temperature overnight. The mixture is diluted with EtOAc and then filtered through a Celite-packed, sintered-glass funnel. The cake is washed with CHCl3 until the washings are colorless. The organic filtrate is washed with aqueous saturated ammonium chloride and water, dried (Na2SO4) and concentrated in vacuo. The crude solid is triturated with ether, filtered and washed with ether to give 0.032 g (71%) of the title compound as a light brown solid. Physical characteristics: mp 201-206° C.; 1H NMR (400 MHz, DMSO-d6) δ4.21, 4.39, 4.54, 5.51, 7.40, 8.52, 9.0, 9.7; IR (drift) 3368, 1660, 1612, 1597, 1551, 1479, 1410, 1397, 1377, 1353, 1256, 1036, 812, 674, 650 cm−1; MS (EI) m/z 382 (M+, 6); HRMS (FAB) m/z 383.0917 (C19H15ClN4O3+H).

Workup

  1. filtrationfiltered through a Celite-packed, sintered-glass funnel
  2. washThe cake is washed with CHCl3 until the washings
  3. washThe organic filtrate is washed with aqueous saturated ammonium chloride and water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude solid is triturated with ether
  7. filtrationfiltered
  8. washwashed with ether

Sources & evidence

ORD record
ord-da7dde9d61d54676b1c421bf8d957cc5
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

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