Trityl chloride → N-[2-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)ethyl]formamide

HRID 349531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349531
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH:11]=[O:12].C(N(CC)CC)C.[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:7][N:6]1[C:2]([NH:1][C:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[C:3]([CH2:8][CH2:9][NH:10][CH:11]=[O:12])[CH:4]=[N:5]1

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 17962016N-[2-(5-amino-1-methylpyrazol-4-yl)ethyl]formamide

Produkt 1

HCID 17962019N-[2-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)ethyl]formamideAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-[2-(5-amino-1-methylpyrazol-4-yl)ethyl]formamide (2.7 g, 16 mmol) and triethylamine (2.5 ml, 17.6 mmol) in methylene chloride (50 ml) was added triphenylmethyl chloride (5.2 g, 17.6 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with successively 10% aqueous citric acid solution and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diisopropyl ether and dried in vacuo to give N-[2-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)ethyl]formamide (4.7 g) as a colorless solid.

Aufarbeitung

  1. washThe reaction mixture was washed with successively 10% aqueous citric acid solution and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with diisopropyl ether
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-760693b07e06409fbc5286b0c00b03ac
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179801B2

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