Trityl chloride → Carbamic acid, N-(2-((((1-methyl-5-((triphenylmethyl)amino)-1H-pyrazol-4-yl)amino)carbonyl)amino)ethyl)-, 1,1-dimethylethyl ester

HRID 1247773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247773
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10].C(N(CC)CC)C.[C:29]1([C:35](Cl)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:18]([O:17][C:15]([NH:14][CH2:13][CH2:12][NH:11][C:9](=[O:10])[NH:8][C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[NH:1][C:35]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 21904481tert-Butyl (2-(3-(5-amino-1-methyl-1H-pyrazol-4-yl)ureido)ethyl)carbamate

Produkt 1

HCID 21904455Carbamic acid, N-(2-((((1-methyl-5-((triphenylmethyl)amino)-1H-pyrazol-4-yl)amino)carbonyl)amino)ethyl)-, 1,1-dimethylethyl esterAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-4-(3-{2-[(tert-butoxycarbonyl)amino]ethyl}ureido)-1-methylpyrazole (597 mg) and triethylamine (243 mg) in methylene chloride (10 ml) was added triphenylmethyl chloride (669 mg), and the mixture was stirred at room temperature for 19 hours. The reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate to give 4-(3-{2-[(tert-butoxycarbonyl)amino]ethyl}ureido)-1-methyl-5-triphenylmethylaminopyrazole (640 mg) as a solid.

Aufarbeitung

  1. washThe reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b2e3fddfb91c4a1187624607ba079527
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129232B2

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