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4-Tert-Butylaniline → N-(4-tert-butyl-phenyl)-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzamide

HRID 38090
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 38090
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19](O)=[O:20])=[N:10][N:11]3[CH2:15][CH2:14][S:13][C:12]=23)=[CH:4][CH:3]=1.[C:25]([C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]>S(Cl)(Cl)=O.C(OCC)(=O)C>[C:25]([C:29]1[CH:30]=[CH:31][C:32]([NH:33][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][CH:24]=[C:16]([C:9]3[C:8]([C:5]4[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=4)=[C:12]4[S:13][CH2:14][CH2:15][N:11]4[N:10]=3)[CH:17]=2)=[CH:34][CH:35]=1)([CH3:28])([CH3:26])[CH3:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 698614-Tert-ButylanilineHCID 674246843-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzoic acid hydrochloride

Produkt 1

HCID 46701906N-(4-tert-butyl-phenyl)-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzamideAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittel
HCID 24386
Thionyl Chloride
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzoic acid hydrochloride (45 mg, 0.125 mmol) was dissolved in thionylchloride (1 mL) and stirred at 60° C. for 1 hour. The solvent was distilled and the residue was taken up with toluene, evaporated to dryness and dried under high vacuum for 1 h. The acid chloride was then dissolved in dry pyridine (1 mL) under nitrogen and 4-tert-butylaniline (0.030 mL, 0.187 mmol, 1.5 eq) was added. The mixture was stirred at room temperature for 1 h and then diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (eluant DCM/EtOH 95:5 to give 44 mg of N-(4-tert-butyl-phenyl)-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzamide as a white solid (77%).

Aufarbeitung

  1. distillationThe solvent was distilled
  2. customevaporated to dryness
  3. customdried under high vacuum for 1 h
  4. dissolutionThe acid chloride was then dissolved in dry pyridine (1 mL) under nitrogen
  5. stirringThe mixture was stirred at room temperature for 1 h
  6. washwashed with saturated aqueous NaHCO3 and brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by chromatography on silica gel (eluant DCM/EtOH 95:5

Quellen und Nachweise

ORD-Eintrag
ord-60819d40753b43e4ad7a8990ed0dc1c1
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08524707B2

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