Triethylamine → 5-isopropyl-1-methyl-1H-indazole-4-carboxylic acid indan-2-yl-(4-methyl-benzyl)-amide

HRID 1591685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1591685
[CH:1]([C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH3:13])[N:8]=[CH:7][C:6]=2[C:5]=1[C:14](Cl)=[O:15])([CH3:3])[CH3:2].[C:17]1(C)[CH:22]=[CH:21][C:20]([NH:23][CH:24]2[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25]2)=[CH:19][CH:18]=1.[CH2:34](N(CC)CC)[CH3:35]>C1COCC1.C(OCC)(=O)C>[CH2:32]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH:24]1[N:23]([CH2:20][C:19]1[CH:18]=[CH:17][C:22]([CH3:21])=[CH:35][CH:34]=1)[C:14]([C:5]1[C:6]2[CH:7]=[N:8][N:9]([CH3:13])[C:10]=2[CH:11]=[CH:12][C:4]=1[CH:1]([CH3:3])[CH3:2])=[O:15]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 15637824HCID 15637824, VerbindungHCID 225669405-Isopropyl-1-methyl-1H-indazole-4-carbonyl chloride

Produkt 1

HCID 207604485-isopropyl-1-methyl-1H-indazole-4-carboxylic acid indan-2-yl-(4-methyl-benzyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Isopropyl-1-methyl-1H-indazole-4-carbonyl chloride (0.618 mmol, 1.0 eq) (30) in 5 ml of THF is added to a solution of (4-tolyl)-indan-2-yl-amine (147 mg, 0.618 mmol) (31) in 5 ml of tetrahydrofuran containing 250 mg of triethylamine at 0° C. The resulting mixture is stirred at room temperature overnight, diluted with 20 ml of ethyl acetate, washed with water and brine, and dried over sodium sulfate. Concentration and purification by silica gel chromatography affords 168 mg of 5-isopropyl-1-methyl-1H-indazole-4-carboxylic acid indan-2-yl-(4-methyl-benzyl)-amide (32). 1H NMR (400 MHz, CDCl3) 7.89 (1H, s), 7.42-6.92 (10H, m), 4.95 (1H, d, J=15.2 Hz), 4.66 (1H, d, J=15.2 Hz), 4.551 (1H, m), 4.05 (3H, s), 3.26-2.73 (5H, m), 2.36 (3H, s), 1.34 (6H, dd, J=1.6, 6.8 Hz). MS (+VE) m/z 438 (M++1).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration and purification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4b178f19fe564207b7520aeeb2d9b1b6
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291621B2

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