Triethylamine → (7-Bromo-1,1-dioxo-1,4-dihydro-1lambda6-pyrido[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester

HRID 548372Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]([NH:8][C:9]1[C:14]([S:15](=[O:18])(=[O:17])[NH2:16])=[CH:13][C:12]([Br:19])=[CH:11][N:10]=1)=O)[CH3:2].C(N(CC)CC)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.CO>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[NH:8][C:9]2[N:10]=[CH:11][C:12]([Br:19])=[CH:13][C:14]=2[S:15](=[O:18])(=[O:17])[N:16]=1)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

In a sealed tube, N-(5-Bromo-3-sulfamoyl-pyridin-2-yl)-malonamic acid ethyl ester (2.2 g, 6.0 mmol) was suspended in toluene (44 mL) and triethylamine (11 mL, 78.9 mmol) was added. The mixture was heated at 110° C. while stirring for 30 min. The solid was completely dissolved, yet an immiscible, oily residue was observed along the bottom of the flask. Upon cooling to 25° C., ethyl acetate (˜50 mL) was added. Everything became miscible. The solution was concentrated in vacuo to afford a golden oil. The oil was dissolved in methanol (˜50 mL) and concentrated in vacuo to afford the crude product, (7-bromo-1,1-dioxo-1,4-dihydro-1λ6-pyrido[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester (2.18 g, >6.0 mmol, 100%, still contained some solvent), as a golden oil. LC-MS (ESI) calcd for C10H10BrN3O4S 346.96, found 348.1 (100%), 349.2 (10%), 350.2 (99%) [M+H+].

Workup

dissolutionThe solid was completely dissolved
temperatureUpon cooling to 25° C.
concentrationThe solution was concentrated in vacuo
customto afford a golden oil
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-701ce1d4d90948358f82e320af51db3f
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939524B2

Reaction notes

Loading…