2,4,6-Trichlorobenzoyl chloride → N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79376

Reaktionsgleichung

Reaktionsgleichung von HRID 79376
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]([O-:22])=O)=[CH:18][N:19]=[C:13]3[CH:12]=2)[CH2:4][CH2:3]1.[Li+].ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[CH3:36][N:37]1[C:41]([CH3:42])=[CH:40][C:39]([CH2:43][N:44]2[C:52]3[CH:51]=[CH:50][CH:49]=[C:48]([NH2:53])[C:47]=3[C:46]([CH2:54][CH3:55])=[N:45]2)=[N:38]1>CN1C(=O)CCC1.[OH-].[Na+].CCOC(C)=O>[CH3:36][N:37]1[C:41]([CH3:42])=[CH:40][C:39]([CH2:43][N:44]2[C:52]3[C:47](=[C:48]([NH:53][C:20]([C:17]4[N:14]5[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:5]6[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]6)=[CH:12][C:13]5=[N:19][CH:18]=4)=[O:22])[CH:49]=[CH:50][CH:51]=3)[C:46]([CH2:54][CH3:55])=[N:45]2)=[N:38]1

Komponenten

7

Edukt 3

HCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 67252742Lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylateHCID 672600441-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amine

Produkt 1

HCID 67261556N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamideAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
87 °C

Versuchsvorschrift

To a solution of lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (89.1 mg, 0.278 mmol) in NMP (6 mL) at 0° C. was added 2,4,6-trichlorobenzoyl chloride (43.5 μL, 0.278 mmol). The reaction mixture was stirred for 30 minutes. 1-((1,5-Dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amine (50 mg, 0.186 mmol) was added and the mixture was heated at 87° C. for 3 hours. The reaction mixture was cooled to ambient temperature, and diluted with 10% NaOH aqueous solution (5 mL) and EtOAc (20 mL). The organic phase was washed with water and brine and then concentrated under reduced pressure. The residue was triturated with Et2O to give final product (71 mg). MS (ES+APCI) m/z=556 (M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washThe organic phase was washed with water and brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-bd91e1da63934e00a5e45de0438dd907
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

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