Methanol → 3'-Fluoro-4'-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methylbiphenyl-4-carboxylic acid

HRID 2356802

反応式

HRID 2356802 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[C:21]([CH3:29])[CH:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.CO.O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[C:21]([CH3:29])[CH:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 59385264Methyl 3'-fluoro-4'-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methylbiphenyl-4-carboxylate

生成物 1

HCID 593852543'-Fluoro-4'-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methylbiphenyl-4-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

As shown in Reaction Scheme 6, methyl 3′-fluoro-4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methylbiphenyl-4-carboxylate (0.38 g, 0.67 mmol) was suspended in THF (5 mL), MeOH (5 mL), and water (2.5 mL), and NaOH (0.27 g, 6.7 mmol) was added. The reaction mixture was heated at 50° C. for 3 h. Upon cooling to rt, the reaction mixture was concentrated in vacuo, acidified with 2N HCl, and the resulting solid was collected by filtration. This yielded 0.33 g (quantitative) of the title compound. 1H NMR (400 MHz, DMSO-d6) 2.62 (s, 3H), 7.10 (t, 1H), 7.49-7.58 (m, 5H), 7.65-7.75 (m, 1H), 8.10 (d, 1H), 8.58 (t, 1H), 10.85 (br, 1H).

後処理

  1. temperatureUpon cooling to rt
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. filtrationthe resulting solid was collected by filtration

出典と根拠

ORDレコード
ord-d9ffd75ffa6a43cba58c75578b9e98da
出典データセット
uspto-grants-2010_07
特許番号
US07759376B2

関連ノート

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