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Hydrochloric Acid → 3-[6-(5-{5-fluoro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid

HRID 1512938
ノート
印刷プレビュー

反応式

HRID 1512938 の反応式
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:27]=[C:26]4[C:22]([C:23]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[CH:24][NH:25]4)=[CH:21][CH:20]=3)[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].Cl>CC(O)C.O>[F:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:27]=[C:26]4[C:22]([C:23]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:24][NH:25]4)=[CH:21][CH:20]=3)[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146084Ethyl 3-[6-(5-{5-fluoro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate

生成物 1

HCID 445470193-[6-(5-{5-fluoro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid収率 21.4%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 3776Isopropanol溶媒

反応条件

温度
70 °C

実験手順

Sodium hydroxide (8 mg) was added to a solution of ethyl 3-[6-(5-{5-fluoro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D110) (60 mg) in iPrOH (5 mL) and water (5 mL). The resulting mixture was heated at 70° C. for 40 mins. Then 0.5 M HCl solution was added until pH was about 6. The solvent was concentrated, and the residue was dissolved in water. The precipitated solid was purified by Mass Directed Auto Prep to afford 3-[6-(5-{5-fluoro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid (E84) (12 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.39 (6H, d), 2.61 (2H, t), 2.96 (2H, t), 5.47 (1H, m), 7.35 (1H, d), 7.72 (2H, d), 8.11 (1H, t), 8.37 (1H, dd), 8.81 (1H, d), 11.23 (1H, d), 12.11 (1H, br s). MS (ES): C21H19FN4O4 requires 410; found 411.2 (M+H+).

後処理

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in water
  3. customThe precipitated solid was purified by Mass Directed Auto Prep

出典と根拠

ORDレコード
ord-d721ecee88af4ab8bdedc01ad8226f27
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08217028B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート