Sulfuric Acid → 4-Amino-2-iodo-thieno[3,2-c]pyridine-7-carboxylic acid amide

HRID 1868296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1868296
[I:1][C:2]1[S:10][C:9]2[C:8]([C:11]#[N:12])=[CH:7][N:6]=[C:5]([NH:13]CC3C=CC(OC)=CC=3)[C:4]=2[CH:3]=1.[OH:23]S(O)(=O)=O>>[NH2:13][C:5]1[C:4]2[CH:3]=[C:2]([I:1])[S:10][C:9]=2[C:8]([C:11]([NH2:12])=[O:23])=[CH:7][N:6]=1

Komponenten

3

Edukt 2

HCID 1118Sulfuric AcidHCID 18446524HCID 18446524, Verbindung

Produkt 1

HCID 569269074-Amino-2-iodo-thieno[3,2-c]pyridine-7-carboxylic acid amide

Versuchsvorschrift

To 2-iodo-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile 27 (3.88 g, 9.21 mmol) was added conc. H2SO4 (9.75 mL). The reaction was stirred for 1 h at room temperature, then quenched by the addition of ice (20 g). The filtered precipitate was washed with H2O, then suspended in 30% MeOH—CH2Cl2 (30 mL). Triethylamine was added dropwise until the solids dissolved. The solution was purified by silica gel column chromatography (eluent: 10 to 20% MeOH in CH2Cl2 with 1% NH4OH additive) to yield 2.6 g of 28. 1H NMR (400 MHz, d6-DMSO) δ 8.46 (s, 1H), 7.94 (m, 2H), 7.31 (bs, 1H), 7.18 (s, 2H).

Aufarbeitung

  1. customquenched by the addition of ice (20 g)
  2. washThe filtered precipitate was washed with H2O
  3. additionTriethylamine was added dropwise until the solids
  4. dissolutiondissolved
  5. customThe solution was purified by silica gel column chromatography (eluent: 10 to 20% MeOH in CH2Cl2 with 1% NH4OH additive)

Quellen und Nachweise

ORD-Eintrag
ord-657daa98f8464f3fb367f9b38ac487e8
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07635695B2

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