Triethylamine → N-(4-chloro-2-cyclopropyl-5-methoxyphenyl)-N-(methylsulfonyl)methanesulfonamide

HRID 705371Notes

Reaction equation

[Cl:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][C:5]([NH2:6])=[C:4]([CH:11]2[CH2:13][CH2:12]2)[CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>O1CCCC1>[Cl:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][C:5]([N:6]([S:22]([CH3:21])(=[O:24])=[O:23])[S:22]([CH3:21])(=[O:24])=[O:23])=[C:4]([CH:11]2[CH2:12][CH2:13]2)[CH:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of Example 18B (1.0 equivalent) and triethylamine (2.3 equivalents) in tetrahydrofuran (0.5 M final concentration based on product from Example 18B) was cooled to 5° C. and treated dropwise with methane sulfonyl chloride (2.3 equivalents) maintaining the temperature below 20° C. After the addition was completed, the reaction mixture was warmed up to ambient temperature for 20 minutes and partitioned with water and methylene chloride. The organic layer was washed with 5% aqueous NaCl solution, dried (Na2SO4), filtered and concentrated. The resulting solid was triturated with isopropyl acetate/heptane (2:1), and the solid was collected by filtration and dried to constant mass (80% yield).

Workup

temperaturemaintaining the temperature below 20° C
additionAfter the addition
temperaturethe reaction mixture was warmed up to ambient temperature for 20 minutes
custompartitioned with water and methylene chloride
washThe organic layer was washed with 5% aqueous NaCl solution
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe resulting solid was triturated with isopropyl acetate/heptane (2:1)
filtrationthe solid was collected by filtration
customdried to constant mass (80% yield)

Sources & evidence

ORD record: ord-e33eaaad12864dd38e5cabf24cb9f47c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173887B2

Reaction notes

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