2-Thiophenesulfonyl chloride → Methyl (4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(2-thienylsulfonyl)-amino]methyl}phenoxy)acetate

HRID 551910

Reaktionsgleichung

Reaktionsgleichung von HRID 551910
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][CH2:19][C:20]3[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[S:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[S:39](Cl)(=[O:41])=[O:40]>N1C=CC=CC=1.Cl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=3)[S:39]([C:35]3[S:34][CH:38]=[CH:37][CH:36]=3)(=[O:41])=[O:40])=[CH:32][CH:33]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 2

HCID 855182-Thiophenesulfonyl chlorideHCID 57554567Methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]phenoxy}acetate

Produkt 1

HCID 11699885Methyl (4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(2-thienylsulfonyl)-amino]methyl}phenoxy)acetateAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cold solution (0° C.) of methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]-phenoxy}acetate (40 mg, 0.091 mmol) in anhydrous pyridine (2 ml) was added 2-thiophenesulfonyl chloride (Aldrich, 82 mg, 0.45 mmol) and the reaction mixture was stirred at 0° C. for 4 hrs and at rt for an additional 15 hours. The reaction mixture was diluted with an aqueous solution of HCl (1N) and extracted with DCM (3×). The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure to give 30 mg (56%) of the title compound as a yellow oil. HPLC, Rt: 5.9 un purity: 92.5%). 1H NMR (CDCl3) δ: 7.61 (dd, J=5.3, 1.5 Hz, 1H), 7.58 (dd, J=3.8, 1.5 Hz, 1H), 7.44 (d, J=8.3 Hz, 2H), 7.39 (d, J=7.9 Hz, 2H), 7.17 (d, J=8.3 Hz, 2H), 7.12 (dd, J=5.3, 3.8 Hz, 1H), 7.04 (m, 4H), 6.78 (d, J=8.7 Hz, 2H), 4.61 (s, 2H), 4.33 (s, 2H), 4.30 (s, 2H), 3.81 (s, 3H), 2.63 (t, J=7.7 Hz, 2H), 1.61 (m, 2H), 1.37 (m, 2H), 0.94 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0c22d0db86ef4e90afa1b71e13884736
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947851B2

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