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Water → methyl 1-methyl-3-({[1-(triphenylmethyl)imidazol-2-yl]amino}methyl)-1H-indazole-6-carboxylate

HRID 2252472
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2252472
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[N:5]([CH3:16])[N:4]=1)=O.[C:17]([N:36]1[CH:40]=[CH:39][N:38]=[C:37]1[NH2:41])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C1(C)C=CC=CC=1>[CH3:16][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=2)[C:3]([CH2:1][NH:41][C:37]2[N:36]([C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:40]=[CH:39][N:38]=2)=[N:4]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 103589742-Amino-1-trityl-imidazoleHCID 22598959methyl 3-formyl-1-methyl-1H-indazole-6-carboxylate

Produkt 1

HCID 22598985methyl 1-methyl-3-({[1-(triphenylmethyl)imidazol-2-yl]amino}methyl)-1H-indazole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

The product of Step A (204 mg, 1 mmol) is dissolved in toluene (10 mL) with N-trityl-2-aminoimidazole (357 mg, 1.1 mmol) and heated to reflux with a Dean-Stark trap. Four aliquots of toluene (3 mL each) are removed via distillation at 1.5 hour intervals, being replaced by dry toluene each time, and then the solution is left to reflux for 18 hours. The reaction is cooled to room temperature and sodium triacetoxyborohydride (1 gram, 5 mmol) is added in one portion. The reaction is stirred at room temperature for 24 hours, poured into water, and the layers separated. The aqueous layer is extracted with ethyl acetate and the combined organic layers are washed with saturated bicarbonate, water, and brine, dried over magnesium sulfate, concentrated, and purified by flash chromatography to afford the product.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux with a Dean-Stark trap
  3. customFour aliquots of toluene (3 mL each) are removed via distillation at 1.5 hour intervals
  4. waitthe solution is left
  5. temperatureto reflux for 18 hours
  6. customthe layers separated
  7. extractionThe aqueous layer is extracted with ethyl acetate
  8. washthe combined organic layers are washed with saturated bicarbonate, water, and brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. custompurified by flash chromatography
  12. customto afford the product

Quellen und Nachweise

ORD-Eintrag
ord-675db744157f4bd094bfc0279d0de5e8
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07321045B2

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