Pyridine → Benzoic acid, 5-ethyl-2-[(phenylsulfonyl)amino]-

HRID 1725865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1725865
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[Si](C)(C)C.N1C=CC=CC=1.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[CH2:11]([C:8]1[CH:9]=[CH:10][C:2]([NH:1][S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])[CH3:12]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 7369Benzenesulfonyl chlorideHCID 77444862-Amino-5-ethylbenzoic acid

Produkt 1

HCID 10402833Benzoic acid, 5-ethyl-2-[(phenylsulfonyl)amino]-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of Example 1C (0.033 g, 0.200 mmol) in dichloromethane (1 mL) was treated with 1M chlorotrimethylsilane in dichloromethane (440 μL, 0.044 mmol) and pyridine (56.6 μL, 0.70 mmol), shaken for 4 hours at ambient temperature, treated with a solution of benzenesulfonyl chloride (0.042 g, 0.24 mmol) in dichloromethane (1 mL), and shaken for 16 hours at ambient temperature. The mixture was concentrated, the residue was acidified to pH 1.0 with 5% aqueous HCl, and the solution was extracted with dichloromethane. The extracts were washed sequentially with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.5 mM ammonium acetate to provide the desired product. MS (ESI(+)) m/e 306 (M+H)+, 323 (M+NH4)+, 328 (M+Na)+; (ESI(−)) m/e 304 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.96 (br s, 1H), 7.78 (d, 2H), 7.73 (d, 1H), 7.64 (m, 1H), 7.55 (m, 2H), 7.42 (m, 2H), 2.54 (q, 2H), 1.10 (t, 3H).

Aufarbeitung

  1. stirringshaken for 16 hours at ambient temperature
  2. concentrationThe mixture was concentrated
  3. extractionthe solution was extracted with dichloromethane
  4. washThe extracts were washed sequentially with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.5 mM ammonium acetate

Quellen und Nachweise

ORD-Eintrag
ord-6e78777a1b3c4b6199705a6af22e4115
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491718B2

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