Ethanethiol, 2-(diethylamino)-, hydrochloride (1:1) → 2-{[(2-{[2-(Diethylamino)ethyl]sulfanyl}phenyl)sulfonyl]amino}-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

HRID 1725995

Reaktionsgleichung

Cl.[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6][SH:7])[CH3:3].[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]>CN(C=O)C>[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6][S: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])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 72.5 °C

Versuchsvorschrift

A suspension of 2-(diethylamino)ethanethiol hydrochloride (560 mg, 3.30 mmol) and 60% sodium hydride dispersion (224 mg, 10.18 mmol) was stirred in 3 mL of dry DMF until hydrogen evolution ceased. The mixture was treated with a solution of 2-([(2-fluorophenyl)sulfonyl]amino)-5,6,7,8-tetrahydro-1-napthalenecarboxylic acid methyl ester (200 mg, 0.55 mmol) in 1 mL of DMF, stirred at 70 to 75° C. overnight, and concentrated. The concentrate was purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product (200 mg, 78.7%). MS (APCI) m/e 462.8 (M+H)+; 1H NMR (400 MHz, CD3OD) δ 7.89 (dd, 1H), 7.65 (dd, 1H), 7.57 (dt, 1H) 7.34 (dt, 1H), 7.18 (d, 1H), 7.00 (d, 1H), 3.34-3.51 (m, 4H), 3.29 (m, 2H), 3.25 (q, 4H), 2.65-2.77 (m, 4H), 1.70 (m, 4H), 1.28 (t, 6H).

Aufarbeitung

concentrationconcentrated
customThe concentrate was purified by C18 reverse-phase

Quellen und Nachweise

ORD-Eintrag: ord-4065f438f60940c7a1a2d9fb6ed086a5
Quelldatensatz: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07491718B2

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