Acetic Acid → 6-(3-{[2-Fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)pyridine-2-carboxylic acid

HRID 1161528ノート

反応式

HRID 1161528 の反応式
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[C:15](=[O:16])[NH:14][C:13]([CH:17]([C:31]3[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:33]([O:39][CH2:40][CH2:41][F:42])[C:32]=3[F:43])[NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[N:29]=[C:28]([CH3:30])[O:27][N:26]=4)=[CH:21][CH:20]=3)=[N:12]2)[N:6]=1)=[O:4].C1COCC1.[OH-].[Na+].C(O)(=O)C>CO>[F:43][C:32]1[C:33]([O:39][CH2:40][CH2:41][F:42])=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:31]=1[CH:17]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:29]=[C:28]([CH3:30])[O:27][N:26]=2)=[CH:21][CH:20]=1)[C:13]1[NH:14][C:15](=[O:16])[N:11]([C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][CH:8]=2)[N:12]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 1361736316-(3-{[2-Fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)pyridine-2-carboxylic acid methyl ester

生成物 1

HCID 1361738316-(3-{[2-Fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)pyridine-2-carboxylic acid収率 49.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

After dissolving 167 mg of 6-(3-{[2-fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)pyridine-2-carboxylic acid methyl ester in 6 ml of a methanol:THF=2:1 mixed solvent, there was added 562 μl of a 5N aqueous sodium hydroxide solution and the mixture was stirred at room temperature for 15 hours. The mixture was adjusted to acidic with acetic acid and then concentrated under reduced pressure. The residue was dissolved in methanol, and the solution was filtered through celite and then purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid) to give the title compound (81 mg) as a light yellow solid.

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol
  3. filtrationthe solution was filtered through celite
  4. custompurified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-76c14ea702e4435cb24fdc3bd87a5de3
出典データセット
uspto-grants-2010_10
特許番号
US07816522B2

反応ノート

読み込み中…