N-{5-[2-Bromo-5-(3-dimethylamino-propylsulfamoyl)-thiophen-3-yl]4-methyl-thiazol-2-yl}-acetamide → N-{5-[5-({[3-(dimethylamino)propyl]amino}sulfonyl)-3-thienyl]4-methyl-1,3-thiazol-2-yl}acetamide

HRID 1948421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948421
Br[C:2]1[S:3][C:4]([S:17](=[O:26])(=[O:25])[NH:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:5][C:6]=1[C:7]1[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=1[CH3:16].C([Li])CCC>C1COCC1>[CH3:24][N:22]([CH3:23])[CH2:21][CH2:20][CH2:19][NH:18][S:17]([C:4]1[S:3][CH:2]=[C:6]([C:7]2[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=2[CH3:16])[CH:5]=1)(=[O:26])=[O:25]

Komponenten

4

Edukt 2

HCID 86623147N-{5-[2-Bromo-5-(3-dimethylamino-propylsulfamoyl)-thiophen-3-yl]4-methyl-thiazol-2-yl}-acetamideHCID 178418339Butyllithium

Produkt 1

HCID 11998677N-{5-[5-({[3-(dimethylamino)propyl]amino}sulfonyl)-3-thienyl]4-methyl-1,3-thiazol-2-yl}acetamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

N-{5-[2-Bromo-5-(3-dimethylamino-propylsulfamoyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}-acetamide obtained in Step I as described above (200 mg; 0.42 mmol; 1 eq), is dissolved in anhydrous THF (50 ml). The reaction mixture is cooled to down to −70° C. and put under nitrogen. n-Butyllithium (2.1 ml; 1.6 M; 3.32 mmol; 8 eq) is added dropwise. After 2 h 30, the reaction is complete and is quenched with water. Solvents are evaporated and the resulting mixture is purified by preparative HPLC affording Compound (27) as a brown oil (120 mg; 68%).

Aufarbeitung

  1. customis quenched with water
  2. customSolvents are evaporated
  3. customthe resulting mixture is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-32df140b888245fcbbb820f67f6216c7
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399497B2

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