(4-Amino-3-sulfamoyl-phenyl)-carbamic acid tert-butyl ester → HCID 136347364, Verbindung

HRID 601386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601386
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[S:16]([NH2:19])(=[O:18])=[O:17].CS[C:22](SC)=[C:23]1[C:32](=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]([NH:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)[C:24]1=[O:39]>O1CCOCC1>[CH:36]1([CH2:35][NH:34][N:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]([OH:33])=[C:23]([C:22]3[NH:1][C:2]4[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[CH:4][C:3]=4[S:16](=[O:17])(=[O:18])[N:19]=3)[C:24]2=[O:39])[CH2:37][CH2:38]1

Komponenten

4

Edukt 2

HCID 59805694(4-Amino-3-sulfamoyl-phenyl)-carbamic acid tert-butyl esterHCID 670636773-[bis(methylthio)methylene]-1-[(cyclopropylmethyl)amino]quinoline-2,4(1H,3H)-dione

Produkt 1

HCID 136347364HCID 136347364, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of the product of Example 414A (78.1 mg, 0.272 mmol) and the product of Example 353B (91.0 mg, 0.272 mmol) in anhydrous dioxane (2.7 mL) was heated under reflux for 3 h. The reaction mixture was then cooled to 25° C. and concentrated under reduced pressure to yield an oily solid. The solid was triturated with methanol to yield the title compound (72.5 mg, 51%). 1H NMR (300 MHz, DMSO-d6) δ 0.14 (d, J=4.04 Hz, 2 H) 0.42 (m, 2 H) 1.00 (m, 1 H) 1.51 (s, 9 H) 2.85 (bd, J=4.78 Hz, 2 H) 6.45 (bs, 1 H) 7.44 (t, J=7.54 Hz, 1 H) 7.62 (d, J=8.82 Hz, 1 H) 7.69 (dd, J=8.82, 2.20 Hz, 1 H) 7.89 (m, J=7.91, 7.91 Hz, 1 H) 8.10 (d, J=8.46 Hz, 1 H) 8.17 (m, 2 H) 9.93 (s, 1 H) 14.08 (s, 1 H) 15.15 (d, J=4.78 Hz, 1 H). MS (ESI−) m/z 524.0 (M−H)−. The sodium salt of the compound was prepared by reacting example 414B (3.9 mg, 0.0074 mmol) with 1 N sodium hydroxide solution (0.0074 mL, 0.0074 mmol) in 0.5 mL water and 0.5 mL tetrahydrofuran at room temperature for 1.2 h. The reaction mixture was then evaporated under a stream of nitrogen to provide the sodium salt (4.1 mg, 100% yield). 1H NMR (300 MHz, DMSO-d6) δ 0.20 (m, J=5.52 Hz, 2 H) 0.46 (d, J=8.82 Hz, 2 H) 1.00 (m, 1 H) 1.50 (s, 9 H) 3.30 (m, 2 H) 5.96 (t, J=6.25 Hz, 1 H) 7.06 (t, J=7.17 Hz, 1 H) 7.20 (d, J=9.19 Hz, 1 H) 7.52 (m, 2 H) 7.67 (d, J=8.82 Hz, 1 H) 7.90 (s, 1 H) 8.06 (d, J=7.35 Hz, 1 H) 9.60 (s, 1 H) 16.22 (s, 1 H). MS (ESI+) m/z 543.1 (M+H+H2O-Na)+, 526.1 (M−Na)+, (ESI−) m/z 524.1 (M−H)−.

Aufarbeitung

  1. temperatureunder reflux for 3 h
  2. concentrationconcentrated under reduced pressure
  3. customto yield an oily solid
  4. customThe solid was triturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-499985f777e84a24946a9f9c8e9b0c67
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902203B2

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