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2-Amino-5-methoxybenzenesulfonamide → HCID 178487340, Verbindung

HRID 2374355
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2374355
C(O[C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[N:9]2[CH:18]=[CH:19][CH:20]=[C:8]2[C:7]=1[OH:21])=O)C.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[S:31]([NH2:34])(=[O:33])=[O:32]>C(O)C>[OH:21][C:7]1[C:8]2[N:9]([CH:18]=[CH:19][CH:20]=2)[N:10]([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[C:11](=[O:12])[C:6]=1[C:4]1[NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[S:31](=[O:32])(=[O:33])[N:34]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 112526652-Amino-5-methoxybenzenesulfonamideHCID 598535874-Hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

Produkt 1

HCID 178487340HCID 178487340, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

4-Hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester (Example 1f, 0.040 g, 0.14 mmol) was mixed with 2-amino-5-methoxy-benzenesulfonamide (Example 2b, 0.0235 g, 0.14 mmol) and the resulting mixture was heated to 180° C. for 20 min. The resulting crude oil was allowed to cool to 25° C. and ethanol (0.5 mL) was added and sonicated to afford a tan precipitate, which was collected and dried in vacuo. The crude solid was dissolved in 1.0 M aqueous potassium hydroxide solution (0.5 mL) and heated to 110° C. for 12 h. The reaction mixture was allowed to cool to 25° C. and 10% aqueous hydrochloric acid solution (0.5 mL) was added and the resulting white precipitate was collected. The crude solid was washed with methanol and dried in vacuo to afford the desired product, 4-hydroxy-3-(7-methoxy-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-1-(3-methyl-butyl)-pyrrolo[1,2-b]pyridazin-2-one (0.027 g, 0.063 mmol, 47% yield) as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 1.07 (6H, d, J=6.4 Hz), 1.69 (1H, m), 1.78 (1H, m), 3.89 (3H, s), 4.39 (2H, t, J=7.6 Hz), 6.60 (1H, dd, J1=4.4 Hz, J2=2.8 Hz), 7.04 (1H, d, J=4.4 Hz), 7.05 (1H, dd, J1=4.8 Hz, J2=2.0 Hz), 7.25 (1H, m), 7.17 (1H, m), 7.39 (1H, d, J=2.0 Hz); LC-MS (ESI) calcd for C19H22N4O5S 430.49. found 431.33 [M+H+].

Aufarbeitung

  1. temperatureto cool to 25° C.
  2. customsonicated
  3. customto afford a tan precipitate, which
  4. customwas collected
  5. customdried in vacuo
  6. dissolutionThe crude solid was dissolved in 1.0 M aqueous potassium hydroxide solution (0.5 mL)
  7. temperatureheated to 110° C. for 12 h
  8. temperatureto cool to 25° C.
  9. addition10% aqueous hydrochloric acid solution (0.5 mL) was added
  10. customthe resulting white precipitate was collected
  11. washThe crude solid was washed with methanol
  12. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9213c7963f9846ee93f7b478cbae5b90
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07462611B2

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