Hydrochloric Acid → {5-Fluoro-2-methyl-1-[4-(morpholine-4-sulfonyl)-benzyl]-1H-indol-3-yl}-acetic acid

HRID 1364586노트

반응식

HRID 1364586 반응식
C([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][C:7]=1[CH3:16])C.[H-].[Na+].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1.Cl>CS(C)=O.O>[F:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:7]([CH3:16])=[C:6]2[CH2:5][C:4]([OH:3])=[O:17]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 27796804-((4-(Bromomethyl)phenyl)sulfonyl)morpholineHCID 11665843Ethyl (5-fluoro-2-methyl-1H-indol-3-yl)acetate

생성물 1

HCID 23627406{5-Fluoro-2-methyl-1-[4-(morpholine-4-sulfonyl)-benzyl]-1H-indol-3-yl}-acetic acid

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

To a stirring suspension of (5-fluoro-2-methyl-1H-indol-3-yl)-acetic acid ethyl ester (100 mg, 0.43 mmol) in dry DMSO (1 ml), is added NaH (29 mg, 0.73 mmol). The reaction mixture is stirred at room temperature for 15 min after which time 4-(4-bromomethyl-benzenesulfonyl)-morpholine (136 mg, 0.43 mmol) is added. The reaction mixture is diluted with water (2 ml) and treated with 1N HCl aq to acidic pH. The crude reaction mixture is purified by reverse phase chromatography on a C18 Isolute™ cartridge (70 g) eluting in 0-100% MeCN in water using a FlashMaster Personal™ and GradMaster™; [M+H]+ 448.

후처리

  1. additionis added
  2. customThe crude reaction mixture
  3. customis purified by reverse phase chromatography on a C18 Isolute™ cartridge (70 g)
  4. washeluting in 0-100% MeCN in water using a FlashMaster Personal™ and GradMaster™

출처 및 근거

ORD 기록
ord-27fcca35f09f47ed82928cc99ad5980f
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888383B2

반응 노트

불러오는 중…