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Ethanol → HCID 178504904, Verbindung

HRID 1257727
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1257727
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:30]([O-])=O)[C:18]([NH:19][C@H:20]4[CH2:25][CH2:24][C@H:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[Cl-].[NH4+]>[Fe].O>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:30])[C:18]([NH:19][C@H:20]4[CH2:21][CH2:22][C@H:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:24][CH2:25]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 178504905HCID 178504905, Verbindung

Produkt 1

HCID 178504904HCID 178504904, VerbindungAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator
HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of trans (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(4-methanesulfonyl-cyclohexyl)-amine (585 mg, 1.20 mmol) and ethanol (4 mL, IMS grade) was treated with water (1.3 mL) followed by ammonium chloride (393 mg, 7.30 mmol) and iron powder (274 mg, 4.90 mmol). The mixture was heated to 80° C. for 45 minutes. The resulting solid was isolated and washed repeatedly with ethanol/water. The filtrate was partially concentrated under vacuum and then diluted with DCM and water. The phases were separated and the aqueous phase was extracted with DCM (×2). The combined organic extracts were washed with brine, dried with sodium sulfate and concentrated under vacuum to give 505 mg (92%) of trans 1-benzenesulfonyl-N*4*-(4-methanesulfonyl-cyclohexyl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine as a pale brown solid that was used without further purification. 1H NMR (400 MHz, DMSO) δ: 8.01 (dd, 2H), 7.70-7.64 (m, 1H), 7.55 (m, 3H), 7.47 (d, 1H), 6.76 (d, 1H), 5.13 (d, 1H), 3.72 (br s, 1H), 3.06 (m, 1H), 2.93 (s, 3H), 2.09 (m, 4H), 1.63 (m, 2H), 1.33 (m, 2H).

Aufarbeitung

  1. customThe resulting solid was isolated
  2. washwashed repeatedly with ethanol/water
  3. concentrationThe filtrate was partially concentrated under vacuum
  4. additiondiluted with DCM and water
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with DCM (×2)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3133c5366a374597a4e1de85c23f90a3
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08461328B2

Notizen zur Reaktion

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