tert-Butanol → HCID 59013924, Verbindung

HRID 907527

Reaktionsgleichung

Reaktionsgleichung von HRID 907527
Cl[C:2]1[C:3]([N:7]2[CH2:12][CH:11]([CH3:13])[NH:10][CH:9]([CH3:14])[CH2:8]2)=[N:4][S:5][N:6]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1CO.C([CH:27](CCC)[O-:28])(C)(C)C.[K+].C(O)(C)(C)C>O>[CH3:14][CH:9]1[NH:10][CH:11]([CH3:13])[CH2:12][N:7]([C:3]2[C:2]([O:28][CH2:27][C:18]3[CH:17]=[CH:16][N:15]=[CH:20][CH:19]=3)=[N:6][S:5][N:4]=2)[CH2:8]1

Komponenten

6

Edukt 4

HCID 6386tert-ButanolHCID 11474PiconolHCID 23710422Potassium tert-butylbutoxideHCID 590139491-(4-Chloro-[1,2,5]thiadiazol-3-yl)-3,5-dimethyl-piperazine

Produkt 1

HCID 59013924HCID 59013924, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-(4-Chloro-[1,2,5]thiadiazol-3-yl)-3,5-dimethyl-piperazine (7.9 g, 34 mmol), pyridinyl-methanol (7.7 g, 70 mmol), potassium tert-butyl butoxide (11.4 g, 101 mmol) and tert-butyl alcohol (100 mL) were combined and stirred at room temperature overnight. The reaction mixture is diluted with H2O (3×) and extracted with EtOAc (3×). The combined EtOAc extractions are washed with sat'd NaHCO3 (3×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo. The crude product is purified by column chromatography (1:1 hexanes:EtOAc, followed by 49:1 EtOAc:triethylamine, followed by 18:1:1 EtOAc:MeOH:triethylamine) to give 4.15 g (40%) of 3,5-dimethyl-1-[4-(pyridin-4-ylmethoxy)-[1,2,5]thiadiazol-3-yl]-piperazine. 1H NMR (CDCl3) 8.62 (d, 2H), 7.30 (d, 2H), 5.48 (s, 2H), 4.07 (m, 2H), 3.03 (m, 2H), 2.51 (m, 2H), 1.12 (d, 6H) ppm. LC-MS (MH+)=306.

Aufarbeitung

  1. extractionextracted with EtOAc (3×)
  2. extractionThe combined EtOAc extractions
  3. washare washed with sat'd NaHCO3 (3×), sat'd NaCl (1×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by column chromatography (1:1 hexanes:EtOAc, followed by 49:1 EtOAc:triethylamine, followed by 18:1:1 EtOAc:MeOH:triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-52f9bd47c74a4486ae169fbcb74c2a81
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013156B2

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