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

HRID 1383334노트

반응식

HRID 1383334 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-e5ceba4b334244c2ab903fb48b9be35a
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255306B1

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