Chloroacetaldehyde → 6-(3-Methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-3-ol

HRID 38099

Reaktionsgleichung

Reaktionsgleichung von HRID 38099
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:11]([SH:14])[NH:12][N:13]=2)[CH:6]=[CH:7][CH:8]=1.Cl[CH2:22][CH:23]=[O:24]>C1COCC1.O.C(OC(=O)C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:11]3[S:14][CH2:22][CH:23]([OH:24])[N:12]3[N:13]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 33ChloroacetaldehydeHCID 178489941HCID 178489941, Verbindung

Produkt 1

HCID 674238586-(3-Methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-3-olAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

5-(3-Methoxy-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol prepared as described in Example 8 (115 mg, 0.406 mmol) was dissolved in a 1:1 THF/water mixture (3 mL). A 55% aqueous solution of chloroacetaldehyde (0.071 mL, 0.609 mmol, 1.5 eq) was added and the mixture was stirred at room temperature for 2 hours. It was then diluted with ethylacetate and washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and evaporated to dryness to give 123 mg (93%) of crude product, which was used without further purification in the following step.

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c64852dab9d24bf9bd55b39536960b19
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524707B2

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