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Diisopropylethylamine → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-(3-fluoroazetidin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79449
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 79449
Cl.[F:2][CH:3]1[CH2:6][NH:5][CH2:4]1.CCN(C(C)C)C(C)C.[CH2:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[NH:27][C:28]([C:30]2[N:34]3[CH:35]=[CH:36][C:37]([CH2:39][CH:40]=O)=[CH:38][C:33]3=[N:32][CH:31]=2)=[O:29])[N:20]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[N:44]=2)[N:19]=1)[CH3:17]>C(Cl)Cl.C(O)(=O)C>[CH2:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[NH:27][C:28]([C:30]2[N:34]3[CH:35]=[CH:36][C:37]([CH2:39][CH2:40][N:5]4[CH2:6][CH:3]([F:2])[CH2:4]4)=[CH:38][C:33]3=[N:32][CH:31]=2)=[O:29])[N:20]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[N:44]=2)[N:19]=1)[CH3:17]
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Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 101250543-fluoroazetidine HydrochlorideHCID 86672219N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxamide

Produkt 1

HCID 67260207N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-(3-fluoroazetidin-1-yl)ethyl)imidazo[1,2-a]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Katalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-fluoroazetidine hydrochloride (61 mg, 0.55 mmol) in DCM (2 mL) was treated at ambient temperature with Hunig's base (0.10 mL, 0.57 mmol). To the hazy solution was added N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxamide (prepared according to (Example 127, Steps A-B; 50 mg, 0.11 mmol) (prepared according to the procedure for Example 127) and the (10 equivalents) was added, followed by 2 drops of glacial acetic acid, and the resulting mixture was stirred at ambient temperature for 16 hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution, and extracted multiple times with DCM and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to preparative thin-layer chromatography on silica, with a 10% MeOH-DCM mixture as eluent to afford the desired product (10 mg) as a white solid. MS (ES+APCI) m/z=512 (M+H) detected.

Aufarbeitung

  1. customprepared
  2. customprepared
  3. additionwas added
  4. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate solution
  5. extractionextracted multiple times with DCM and EtOAc
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ee324808184f47d98f8efca868d0ef89
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08841455B2

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