Sodium Iodide → 2-[({2-[3-(Diethylamino)propoxy]phenyl}sulfonyl)amino]-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

HRID 1726006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1726006
[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][CH2:6][OH:7])[CH3:2].[H-].[Na+].[H][H].C[O:15][C:16]([C:18]1[C:27]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[CH:21]=[CH:20][C:19]=1[NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1F)(=[O:31])=[O:30])=[O:17].[I-].[Na+]>CN(C=O)C>[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][CH2:6][O:7][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[S:29]([NH:28][C:19]1[CH:20]=[CH:21][C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][C:27]=2[C:18]=1[C:16]([OH:17])=[O:15])(=[O:30])=[O:31])[CH3:2]

Komponenten

7

Edukt 5

HCID 5238Sodium IodideHCID 121593-(Diethylamino)-1-propanolHCID 24758Sodium hydrideHCID 11710286Methyl 2-{[(2-fluorophenyl)sulfonyl]amino}-5,6,7,8-tetrahydro-1-naphthalenecarboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 116339952-[({2-[3-(Diethylamino)propoxy]phenyl}sulfonyl)amino]-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acidAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
72.5 °C

Versuchsvorschrift

A solution of 3-diethylamino-1-propanol (217 mg, 1.65 mmol) in 1 mL dry DMF was added dropwise to 60% sodium hydride dispersion (55 mg, 1.38 mmol). The mixture was stirred until hydrogen evolution ceased. To this mixture was added a solution of 2-([(2-fluorophenyl)sulfonyl]amino)-5,6,7,8-tetrahydro-1-napthalenecarboxylic acid methyl ester (100 mg, 0.28 mmol) in 1 mL of DMF. The mixture was stirred at 70 to 75° C. for three days, concentrated, and dissolved in 2 mL of pyridine. The mixture was treated with 3 equivalents of sodium iodide, heated in a microwave reactor at 150° C. for 25 minutes, and concentrated. The concentrate was purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product (36 mg, 57.1%). MS (APCI): m/e 461.3 (M+H)+; 1H NMR (400 MHz, CD3OD) δ 7.74 (dd, 1H), 7.54 (dt, 1H), 7.27 (d, 1H) 7.12 (d, 1H), 6.98-7.04 (m, 2H), 4.27 (t, 2H), 3.43-3.51 (m, 2H), 3.25-3.36 (m, 6H), 3.65-3.81 (m, 4H), 3.35 (m, 2H), 1.70 (m, 4H), 1.37 (t, 6H).

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutiondissolved in 2 mL of pyridine
  3. temperatureheated in a microwave reactor at 150° C. for 25 minutes
  4. concentrationconcentrated
  5. customThe concentrate was purified by C18 reverse-phase

Quellen und Nachweise

ORD-Eintrag
ord-126d57a4f9ba407d831d0e145a818fbc
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491718B2

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