Cesium carbonate → methyl 2-chloro-4-(N-(2-morpholinoethyl)methylsulfonamido)benzoate

HRID 633137Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:16][C:17]1[CH:26]=[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]>CN(C=O)C>[Cl:16][C:17]1[CH:26]=[C:25]([N:27]([CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)[S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

Conditions

Temperature: 150 °C

Procedure

1.2 g of 4-(2-chloroethyl)morpholine and 2.5 g of Cesium Carbonate were added to 334 mg of methyl 2-chloro-4-(methylsulfonamido)benzoate in 7 mL of DMF and stirred in the microwave at 150° C. for 30 minutes. The reaction mixture was extracted in Ethyl Acetate twice with water, dried over Magnesium Sulfate, filtered, concentrated to give crude methyl 2-chloro-4-(N-(2-morpholinoethyl)methylsulfonamido)benzoate. 476 mg of methyl 2-chloro-4-(N-(2-morpholinoethyl)methylsulfonamido)benzoate was hydrolyzed via Procedure M and purified by reverse phase HPLC to yield 460 mg of crude 2-chloro-4-(N-(2-morpholinoethyl)methylsulfonamido)benzoic acid. 100 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 2-chloro-4-(N-(2-morpholinoethyl)methylsulfonamido)benzoic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(N-(2-morpholinoethyl)methylsulfonamido)benzamide. MS (Q1) 549 (M)+.

Workup

extractionThe reaction mixture was extracted in Ethyl Acetate twice with water
dry with materialdried over Magnesium Sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-c94e8e36e4274b9da90e2cd6cd069535
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321761B2

Reaction notes

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