Potassium Carbonate → 4-[(3-chloro-4-cyanophenoxy)methyl]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

HRID 1525649노트

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HRID 1525649 반응식
Br[CH2:2][C:3]1[C:17]([F:18])=[CH:16][C:6]([C:7]([NH:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[O:8])=[C:5]([F:19])[CH:4]=1.[Cl:20][C:21]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:22]=1[C:23]#[N:24].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl.O>[Cl:20][C:21]1[CH:28]=[C:27]([CH:26]=[CH:25][C:22]=1[C:23]#[N:24])[O:29][CH2:2][C:3]1[C:17]([F:18])=[CH:16][C:6]([C:7]([NH:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[O:8])=[C:5]([F:19])[CH:4]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 896195864-(Bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

생성물 1

HCID 716161464-[(3-chloro-4-cyanophenoxy)methyl]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-(bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide (Preparation 1, 33 mg, 0.092 mmol) in DMSO (1 mL) was added 2-chloro-4-hydroxybenzonitrile (114 mg, 0.092 mmol) and K2CO3 (25 mg, 0.18 mmol). The reaction was stirred at room temperature for 16 hours. The reaction was diluted with DCM (10 mL) and water (20 mL). The organic layer was separated and the aqueous layer extracted with DCM (2×10 mL). The combined organic layers were filtered through a phase separation cartridge and reduced to dryness to give a yellow oil which was purified by reverse phase preparative HPLC to afford the title compound.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with DCM (2×10 mL)
  3. filtrationThe combined organic layers were filtered through a phase separation cartridge
  4. customto give a yellow oil which
  5. customwas purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-5ea0b19e71e34514a5071bc35779f6c6
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085517B2

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