Triethylamine → HCID 19108400, compound

HRID 327386Notes

Reaction equation

[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH3:13])[CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[CH3:27][N:28]([CH2:30][CH:31]1[CH:36]([NH2:37])[CH:35]2[CH2:38][CH2:39][N:32]1[CH2:33][CH2:34]2)[CH3:29]>C(Cl)Cl>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:37][CH:36]2[CH:35]3[CH2:38][CH2:39][N:32]([CH2:33][CH2:34]3)[CH:31]2[CH2:30][N:28]([CH3:29])[CH3:27])=[O:8])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

Conditions

Temperature: -55 °C

Procedure

A solution of 4-amino-5-chloro-2-methoxybenzoic acid (2.22 g, 11 mmoles) and triethylamine (1.12 g, 11 mmoles) in anhydrous methylene chloride (35 ml) under nitrogen was cooled (0° C.) and treated dropwise with ethyl chloroformate (1.2 g, 11 mmoles). After 45 minutes at 0° C., the solution was cooled (-55° C.) and treated dropwise with 2-(dimethylaminomethyl)-1-azabicyclo[2.2.2]octan-3-amine (2.11 g, 11.5 mmoles) in 7 ml of methylene chloride. The solution was warmed to 25° C. over one hour, stirred for one hour, and diluted with methylene chloride to a total volume of 100 ml. The organic solution was washed with 1.0N sodium hydroxide (2×35 ml), saturated aqueous sodium bicarbonate (35 ml), and brine (35 ml), dried (Na2SO4), and concentrated in vacuo to provide 2.94 g (73%) of an oil.

Workup

temperatureThe solution was warmed to 25° C. over one hour
washThe organic solution was washed with 1.0N sodium hydroxide (2×35 ml), saturated aqueous sodium bicarbonate (35 ml), and brine (35 ml)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-534970f104394443a3f05976bfa2aec8
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05273972

Reaction notes

Loading…