Sodium Bicarbonate → HCID 57541251, compound

HRID 421735Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([CH:18]([S:23]([N:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])C(OC)=O)[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.C(=O)([O-])O.[Na+]>CC(O)=O.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([CH2:18][S:23]([N:26]([CH3:28])[CH3:27])(=[O:24])=[O:25])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl (3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)[(dimethylamino)sulfonyl]acetate (2.04 g, 4.85 mmol) was dissolved in a mixture of AcOH (24.24 ml) and 6M HCl (24.24 ml) and heated to 100° C. for 3 h. The solution was then cooled to room temperature, basified with saturated aqueous sodium hydrogen carbonate and extracted with dichloromethane (3×50 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/Hexanes gradient) to afford the title compound as a yellow solid. 1H NMR (600 MHz, DMSO-D6) δ 8.99 (d, 1H); 8.48 (d, 1H); 8.21 (s, 1H); 7.84 (m, 2H); 7.49 (d, 1H); 7.33 (d, 1H); 4.63 (s, 2H); 2.74 (s, 6H). LRMS (APCI) calculated for C17H16ClN2O3S [M+H]+, 363.1; found 363.1.

Workup

temperatureThe solution was then cooled to room temperature
extractionextracted with dichloromethane (3×50 mL)
dry with materialThe combined organics were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (EtOAc/Hexanes gradient)

Sources & evidence

ORD record: ord-13430bcba721471f92ef4a096a4c73df
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101603B2

Reaction notes

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