Pyridine → 6-Fluoro-5-methanesulfonylamino-N-methyl-N-propyl-isophthalamic acid ethyl ester

HRID 732582Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:17]([F:18])=[C:16]([NH2:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:17]([F:18])=[C:16]([NH:19][S:28]([CH3:27])(=[O:30])=[O:29])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 5-amino-6-fluoro-N-methyl-N-propyl-isophthalamic acid ethyl ester (0.162 g, 0.58 mmol) in dichloromethane (1.5 mL). Cool to 0° C. Add pyridine (51.2 μL, 0.63 mmol) and methanesulfonyl chloride (44.5 μL, 0.58 mmol) to the solution. Allow the reaction to warm to room temperature and stir for 2 days. Quench with water (10 mL) and extract with dichloromethane (2×30 mL). Combine the organic layers and wash with saturated aqueous sodium chloride (20 mL), dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 40:60 ethyl acetate:dichloromethane) to give the title compound as a solid (157 mg, 76%).

Workup

customthe reaction
temperatureto warm to room temperature
customQuench with water (10 mL)
extractionextract with dichloromethane (2×30 mL)
washCombine the organic layers and wash with saturated aqueous sodium chloride (20 mL)
dry with materialdry (magnesium sulfate)
concentrationconcentrate
custompurify
wash(silica gel chromatography, eluting with 40:60 ethyl acetate:dichloromethane)

Sources & evidence

ORD record: ord-cea69a8c65e944e4b87a49017a9acb94
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585885B2

Reaction notes

Loading…