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

HRID 633137
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HRID 633137 반응식
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]
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 767274-(2-Chloroethyl)morpholineHCID 54238017Methyl 2-chloro-4-(methylsulfonamido)benzoate

생성물 1

HCID 66878145methyl 2-chloro-4-(N-(2-morpholinoethyl)methylsulfonamido)benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

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)+.

후처리

  1. extractionThe reaction mixture was extracted in Ethyl Acetate twice with water
  2. dry with materialdried over Magnesium Sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c94e8e36e4274b9da90e2cd6cd069535
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321761B2

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