Triethylamine → HCID 22254499, compound

HRID 1611758Notes

Reaction equation

HRID 1611758 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:10]=2[N:9]=[CH:8]1)#[C:2][CH3:3].I[C:32]1[CH:33]=[C:34]([S:39]([NH2:42])(=[O:41])=[O:40])[CH:35]=[CH:36][C:37]=1[CH3:38].[CH2:43](N(CC)CC)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.C(#N)C>[CH3:38][C:37]1[CH:36]=[CH:35][C:34]([S:39]([NH:42][CH3:43])(=[O:41])=[O:40])=[CH:33][C:32]=1[C:3]#[C:2][CH2:1][O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:10]=2[N:9]=[CH:8]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 13444848HCID 13444848, compoundHCID 22254451HCID 22254451, compound

Product 1

HCID 22254499HCID 22254499, compoundYield 62.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

Under a nitrogen atmosphere benzyl N-{1-[2-(propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-yl}carbamate (0.37 g, 0.91 mmol), 3-iodo-4-methyl-1-benzenesulfonamide (0.3 g, 0.96 mmol), triethylamine (0.2 mL, 1.36 mmol) and anhydrous acetonitrile (20 mL) were combined. Dichlorobis(triphenylphosphine)palladium(II) (13 mg, 0.018 mol) and copper(I) iodide (7 mg, 0.036 mmol) were added and the reaction solution was heated to ˜45° C. After 3 hours analysis by reverse phase HPLC indicated that the reaction was complete. The reaction solution was concentrated under reduced pressure and the residue was purified by flash chromatography (98/2 to 95/5 dichloromethane/methanol) to provide 0.33 g of benzyl N-(1-{2-[(3-{2-methyl-5-[(methylamino)sulfonyl]phenyl}-2-propynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-yl)carbamate as a pale yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (98/2 to 95/5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-12e1b6f3d9a642798dfa49087c1a0405
Source dataset
uspto-grants-2006_01
Patent number
US06989389B2

Reaction notes

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