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Sodium Nitrite → N-(3-Amino-2-tert-butyl-1H-indol-5-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 1964405
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1964405
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[NH:21][C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[N:29]([O-])=O.[Na+]>CC(O)=O.O>[NH2:29][C:19]1[C:18]2[C:22](=[CH:23][CH:24]=[C:16]([NH:15][C:13]([C:10]3([C:8]4[CH:7]=[CH:6][C:5]5[O:1][CH2:2][O:3][C:4]=5[CH:9]=4)[CH2:12][CH2:11]3)=[O:14])[CH:17]=2)[NH:21][C:20]=1[C:25]([CH3:28])([CH3:27])[CH3:26]
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Komponenten

5

Edukt 2

HCID 23668193Sodium NitriteHCID 247629031-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1H-indol-5-yl)cyclopropanecarboxamide

Produkt 1

HCID 59129316N-(3-Amino-2-tert-butyl-1H-indol-5-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1H-indol-5-yl)cyclopropane carboxamide (50 mg, 0.13 mmol) was dissolved in AcOH (2 mL) and warmed to 45° C. To the mixture was added a solution of NaNO2 (9 mg) in H2O (0.03 mL). The mixture was allowed to stir for 30 min at 45° C. before the precipitate was collected and washed with Et2O. This material was used in the next step without further purification. To the crude material, 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-3-nitroso-1H-indol-5-yl)cyclopropanecarboxamide, was added AcOH (2 mL) and Zn dust (5 mg). The mixture was allowed to stir for 1 h at ambient temperature. EtOAc and H2O were added to the mixture. The layers were separated and the organic layer was washed with sat. aq. NaHCO3, dried over MgSO4, and concentrated in vacuo. The residue was taken up in DMF (1 mL) and was purified using prep-HPLC. LCMS: m/z 392.3; retention time of 2.18 min.

Aufarbeitung

  1. customwas collected
  2. washwashed with Et2O
  3. customThis material was used in the next step without further purification
  4. additionTo the crude material, 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-3-nitroso-1H-indol-5-yl)cyclopropanecarboxamide, was added AcOH (2 mL) and Zn dust (5 mg)
  5. stirringto stir for 1 h at ambient temperature
  6. additionEtOAc and H2O were added to the mixture
  7. customThe layers were separated
  8. washthe organic layer was washed with sat. aq. NaHCO3
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-4608ee82aa724c88881eedffc3aa9c1a
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415387B2

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