Triethylamine → N-{5-[5-({[2-(Dimethylamino)ethyl]amino}sulfonyl)-2-thienyl]-4-methyl-1,3-thiazol-2-YL}acetamide

HRID 1948395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948395
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH2:24].C(N(CC)CC)C>C(Cl)Cl>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH:24][S:16]([C:14]1[S:15][C:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:18])=[O:17]

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 66053N,N-Dimethylethylenediamine2×HCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Produkt 1

HCID 11998303N-{5-[5-({[2-(Dimethylamino)ethyl]amino}sulfonyl)-2-thienyl]-4-methyl-1,3-thiazol-2-YL}acetamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step II of Example 1 (1000 mg; 2.97 mmol; 1 eq) is dissolved in anhydrous DCM (100 ml). The reaction is put under nitrogen. 2-Dimethylaminoethylamine (0.97 ml; 8.91 mmol; 3 eq), triethylamine (1.66 ml; 11.9 mmol; 4 eq) are added successively and the reaction mixture is stirred overnight at room temperature. After 15 hours, to complete the reaction, triethylamine (4 eq) and 2-dimethylaminoethylamine (3 eq) are added. After one hour the reaction is complete. The reaction mixture is then wash with NH4Cl sat. (twice) and brine. The organic layer is dried over MgSO4 and the solvents are evaporated. The resulting crude product is dissolved in DCM and extracted with HCl 1N. The aqueous phase is washed with DCM (3 times) and basified with NaOH 5N until pH 10. The desired product is extracted with EtOAc (3 times). Combined organic phases are dried over MgSO4, filtrated and evaporated, affording Compound (3) as a beige solid (480 mg; 40%).

Aufarbeitung

  1. waitAfter 15 hours
  2. additionare added
  3. waitAfter one hour the reaction is complete
  4. washThe reaction mixture is then wash with NH4Cl sat. (twice) and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. customthe solvents are evaporated
  7. dissolutionThe resulting crude product is dissolved in DCM
  8. extractionextracted with HCl 1N
  9. washThe aqueous phase is washed with DCM (3 times)
  10. extractionThe desired product is extracted with EtOAc (3 times)
  11. dry with materialCombined organic phases are dried over MgSO4
  12. filtrationfiltrated
  13. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7a3b97f83848449a8e689e6cce22d5e9
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399497B2

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