Salicylamide → HCID 68850159, compound

HRID 2112925Notes

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(OC([N:37]1[CH2:42][CH2:41][N:40]([C:43]2[C:48]3[N:49]([CH2:54][C:55]#[C:56][CH3:57])[C:50](=[O:53])[N:51]([CH3:52])[C:47]=3[C:46](Br)=[CH:45][N:44]=2)[CH2:39][CH2:38]1)=O)(C)(C)C.[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62]>CN1CCCC1=O.[Cu]Cl.ClCCl>[F:59][C:60]([F:65])([F:64])[C:61]([OH:63])=[O:62].[CH2:54]([N:49]1[C:48]2[C:43]([N:40]3[CH2:39][CH2:38][NH:37][CH2:42][CH2:41]3)=[N:44][CH:45]=[C:46]([O:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1]([NH2:10])=[O:9])[C:47]=2[N:51]([CH3:52])[C:50]1=[O:53])[C:55]#[C:56][CH3:57]

Participants

Conditions

Temperature: 130 °C

Procedure

Salicylamide (0.030 g), cesium carbonate (0.071 g), 2,2,6,6-tetramethyl-3,5-heptanedione (0.003 mL), and copper(I) chloride (0.006 g) were added to a solution of 4-[7-bromo-3-(2-butynyl)-1-methyl-2-oxo-2,3-dihydro-1H-imidazo[4.5-c]pyridin-4-yl]-piperazine-1-carboxylic acid t-butyl ester (0.050 g) in 1-methyl-2-pyrrolidone (1 mL). This was heated under nitrogen atmosphere at 130° C. for 14 hours. The reaction solution was cooled, dichloromethane (2 mL) and trifluoroacetic acid (3 mL) were added, and this was stirred for two hours. The solvent was removed by concentration under reduced pressure, and the residue was purified by reverse phase high performance liquid chromatography to give the title compound (0.007 g).

Workup

temperatureThe reaction solution was cooled
customThe solvent was removed by concentration under reduced pressure
customthe residue was purified by reverse phase high performance liquid chromatography

Sources & evidence

ORD record: ord-580ddd8ae4444c8a988561fbeac9b1ca
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524847B2

Reaction notes

Loading…