Hydrochloric Acid → 6-Chloro-16-thia-2,4,8,15,23-pentaazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene 16,16-dioxide

HRID 541810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541810
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[C:22](Cl)[N:21]=3)[CH:14]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl>COCCO.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[Cl:26][C:25]1[CH:24]=[N:23][C:22]2[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH:3]=3)[S:8](=[O:10])(=[O:9])[NH:11][CH2:12][C:13]3[CH:14]=[C:15]([NH:19][C:20]=1[N:21]=2)[CH:16]=[CH:17][CH:18]=3

Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 579626943-Amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzenesulfonamide

Produkt 1

HCID 579622376-Chloro-16-thia-2,4,8,15,23-pentaazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene 16,16-dioxide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 80192-MethoxyethanolLösungsmittelHCID 10340Sodium CarbonateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 3-amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzenesulfonamide (38.0 mg, 0.089 mmol) in 2-methoxyethanol (0.49 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (45 μL). The resulting mixture was heated at 150° C. in the microwave for 15 min. The mixture was diluted with Na2CO3 (aq), extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the crude, which was purified by Combi-Flash column chromatography (4 g column, 0 to 50% EtOAc in Hex) to the desired product as a white powder (7 mg, 20%). LCMS for C17H14ClN5O2S (M+H)+: m/z=388.0, 390.0. 1H NMR (400 MHz, CD3OD): δ 7.62 (m, 1H), 7.54 (s, 1H), 7.28 (t, J=2.0 Hz, 1H), 7.08 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 6.78 (t, J=8.0 Hz, 1H), 6.35 (m, 1H), 6.18 (ddd, J=8.0, 1.6, 1.0 Hz, 1H), 5.98 (m, 1H), 5.82 (ddd, J=7.6, 2.0, 1.0, 1H), 4.20 (s, 2H).

Aufarbeitung

  1. extractionextracted with EtOAc three times
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude, which
  6. customwas purified by Combi-Flash column chromatography (4 g column, 0 to 50% EtOAc in Hex) to the desired product as a white powder (7 mg, 20%)

Quellen und Nachweise

ORD-Eintrag
ord-d09e1aa625fa4b868ea34a783a8c668f
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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