Salicylamide → HCID 57642865, compound

HRID 2112917Notes

Reaction equation

HRID 2112917 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C.[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][N:40]([C:43]2[C:48]3[N:49]([CH2:62][C:63]4[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=4)[C:50](=[O:61])[N:51]([CH2:52][C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=4[C:59]#[N:60])[C:47]=3[C:46](Br)=[CH:45][N:44]=2)[CH2:39][CH2:38]1)=[O:36])([CH3:33])([CH3:32])[CH3:31]>CN1CCCC1=O.[Cu]Cl.COC(C)(C)C>[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][N:40]([C:43]2[C:48]3[N:49]([CH2:62][C:63]4[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=4)[C:50](=[O:61])[N:51]([CH2:52][C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=4[C:59]#[N:60])[C:47]=3[C:46]([O:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:9])[NH2:10])=[CH:45][N:44]=2)[CH2:39][CH2:38]1)=[O:36])([CH3:33])([CH3:31])[CH3:32]

Participants

8

Reactant 4

HCID 5147SalicylamideHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 57642829HCID 57642829, compound

Product 1

HCID 57642865HCID 57642865, compoundYield 17.1%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
130 °C

Procedure

Salicylamide (0.056 g), cesium carbonate (0.130 g), 2,2,6,6-tetramethyl-3,5-heptanedione (0.005 mL), and copper(I) chloride (0.010 g) were added to a solution of 4-[3-benzyl-7-bromo-1-(2-cyanobenzyl)-2-oxo-1H-imidazo[4.5-c]pyridin-4-yl]-piperazine-1-car boxylic acid t-butyl ester (0.123 g) in 1-methyl-2-pyrolidone (2 mL). This was then heated at 130° C. for 22 hours under a nitrogen atmosphere. The reaction solution was cooled, t-butyl methyl ether was added, and this was filtered through celite. The celite was washed with ethyl acetate (25 mL), and the organic layers were combined, and then washed sequentially with 2 N hydrochloric acid (10 mL), 0.5 N hydrochloric acid (10 mL), 1 N aqueous sodium hydroxide solution (10 mL), and saturated aqueous sodium chloride solution (10 mL). This was then dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase high performance liquid chromatography to give the title compound (0.023 g).

Workup

  1. temperatureThe reaction solution was cooled
  2. filtrationthis was filtered through celite
  3. washThe celite was washed with ethyl acetate (25 mL)
  4. washwashed sequentially with 2 N hydrochloric acid (10 mL), 0.5 N hydrochloric acid (10 mL), 1 N aqueous sodium hydroxide solution (10 mL), and saturated aqueous sodium chloride solution (10 mL)
  5. dry with materialThis was then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by reverse phase high performance liquid chromatography

Sources & evidence

ORD record
ord-c05ca667ce79477784af885b09ada1c8
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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