Benzenesulfonyl chloride → ethyl (6-iodo-3-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate

HRID 706484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706484
[I:1][C:2]1[CH:3]=[C:4]([NH:28][C:29]([NH:31][C:32](=[O:36])[O:33][CH2:34][CH3:35])=S)[C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[C:12]([O:26][CH3:27])[CH:11]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.C1(S(Cl)(=O)=O)C=CC=CC=1>O1CCCC1>[CH2:34]([O:33][C:32](=[O:36])[NH:31][C:29]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[C:12]([O:26][CH3:27])[CH:11]=2)[C:5]2=[N:6][CH:7]=[C:2]([I:1])[CH:3]=[C:4]2[N:28]=1)[CH3:35]

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 118114077ethyl N-({5-iodo-2-[({3-methoxy-4-[(4-methoxyphenyl)methoxy]phenyl}methyl)amino]pyridin-3-yl}carbamothioyl)carbamate

Produkt 1

HCID 131733013ethyl (6-iodo-3-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamateAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl N-({5-iodo-2-[({3-methoxy-4-[(4-methoxyphenyl)methoxy]phenyl}methyl)amino]pyridin-3-yl}carbamothioyl)carbamate (2.30 g, 3.69 mmol) and triethylamine (1.30 g, 1.8 mL, 12.85 mmol) in tetrahydrofuran (20 mL) was added benzenesulfonyl chloride (0.93 g, 5.27 mmol). The resulting mixture was allowed to stir at room temperature. After 12 h, a precipitate had formed. The mixture was filtered, and the filtercake was washed with water (2×10 mL) and methanol (10 mL). The solids were dried to provide 1.50 g (69%) of ethyl(6-iodo-3-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate as a brown solid.

Aufarbeitung

  1. customa precipitate had formed
  2. filtrationThe mixture was filtered
  3. washthe filtercake was washed with water (2×10 mL) and methanol (10 mL)
  4. customThe solids were dried

Quellen und Nachweise

ORD-Eintrag
ord-4b134d9de4464665997c28549d03c888
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174986B2

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