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

HRID 1364586ノート

反応式

HRID 1364586 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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™

出典と根拠

ORDレコード
ord-27fcca35f09f47ed82928cc99ad5980f
出典データセット
uspto-grants-2011_02
特許番号
US07888383B2

反応ノート

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