Pyridine → N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(dimethylamino)methyl]benzamide

HRID 2382905

Reaktionsgleichung

Reaktionsgleichung von HRID 2382905
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[C:12]([NH2:14])[N:13]=[C:9]3[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[CH:6]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1.[CH3:25][N:26]([CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH3:27]>ClCCl>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[C:12]([NH:14][C:33](=[O:34])[C:32]4[CH:36]=[CH:37][C:29]([CH2:28][N:26]([CH3:25])[CH3:27])=[CH:30][CH:31]=4)[N:13]=[C:9]3[CH:8]=[C:7]([C:15]([F:16])([F:17])[F:18])[CH:6]=2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 137489654-(N,N-dimethylaminomethyl) benzoyl chlorideHCID 59437445N5-cyclopropyl-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine

Produkt 1

HCID 59437472N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(dimethylamino)methyl]benzamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a reaction vessel containing N5-cyclopropyl-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine ((A18), 77 mg, 0.3 mmol, 1 eq.) and pyridine (0.063 mL, 1.2 mmol, 4 eq.) in dichloromethane (1 mL) was added 4-dimethylaminomethyl-benzoyl chloride (118 mg, 0.6 mmol, 2 eq.) as a solution in dichloromethane (2 mL), dropwise. The vessel was capped and heated to reflux for approximately 16 hours. The reaction mixture was cooled and the solvent removed in vacuo. The residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a white solid (65.1 mg, 52%). HPLC, Rt: 2.59 min (purity: 100%). LC/MS M+(ESI): 419.2, M−(ESI) 417.2.

Aufarbeitung

  1. customThe vessel was capped
  2. temperatureheated
  3. temperatureto reflux for approximately 16 hours
  4. temperatureThe reaction mixture was cooled
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue dissolved in DMSO (1.5 mL)
  7. custompurified by reverse phase preparatory HPLC

Quellen und Nachweise

ORD-Eintrag
ord-21e668023a2d44a6ae77f996b98c7ab0
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263595B2

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