Tetrahydrofuran → 4-(4-Methylpiperazin-1yl)indole-2-carboxylic acid

HRID 1383334ノート

反応式

HRID 1383334 の反応式
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[CH:11]=[CH:10][CH:9]=2)=[O:5])C.O.[OH-].[Li+].O1CCCC1>O>[CH3:21][N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]3)[CH2:16][CH2:17]1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 155502451-(2-(ethoxycarbonyl)-1H-indol-4-yl)-4-methylpiperazine

生成物 1

HCID 211875904-(4-Methylpiperazin-1yl)indole-2-carboxylic acid収率 49%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 1-(2-(ethoxycarbonyl)-1H-indol-4-yl)-4-methylpiperazine (0.91 g, 3.17 mmol), lithium hydroxide hydrate (0.136 g, 3.17 mmol, 1.0 equivalent), tetrahydrofuran (20 mL), and water (4 mL) was heated at reflux under nitrogen for 16 hours. The resulting reaction mixture was evaporated under reduced pressure, and the residue was chromatographed using silica gel (approximately 30 g) and elution with methylene chloride/methanol/ammonium hydroxide [3:2:0.2] to afford the title compound (0.40 g, 1.54 mmol, 49%) as a white solid: mp, 272-273° C.; R, =0.05 in methylene chloride/methanol/ammonium hydroxide [5:1:0.1]; 13C NMR (D2O) δ169.4, 145.0, 137.5, 132.9, 124.7, 120.7, 108.2, 107.3, 103.7, 58.7, 53.7, 51.0; LRMS (m/z, relative intensity) 260 (18), 259 (M+, 100), 244 (9), 215 (7), 170 (24); HRMS calculated for C14H17N3O2 259.1322, found 259.1325.

後処理

  1. temperatureat reflux under nitrogen for 16 hours
  2. customThe resulting reaction mixture
  3. customwas evaporated under reduced pressure
  4. customthe residue was chromatographed
  5. washsilica gel (approximately 30 g) and elution with methylene chloride/methanol/ammonium hydroxide [3:2:0.2]

出典と根拠

ORDレコード
ord-e5ceba4b334244c2ab903fb48b9be35a
出典データセット
uspto-grants-2001_07
特許番号
US06255306B1

反応ノート

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