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Ammonium Chloride → HCID 178492824, Verbindung

HRID 238209
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 238209
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([C:20]3[N:29]([CH3:30])[C:28](=[O:31])[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:32]#[N:33])[CH:26]=4)[N:21]=3)[CH3:19])[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:13][CH2:14][N:15]([CH:18]([C:20]3[N:29]([CH3:30])[C:28](=[O:31])[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:32]5[NH:36][N:35]=[N:34][N:33]=5)[CH:26]=4)[N:21]=3)[CH3:19])[CH2:16][CH2:17]2)(=[O:10])=[O:11])=[CH:7][CH:8]=1
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Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 599931892-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-4-oxo-3,4-dihydro-quinazoline-6-carbonitrile

Produkt 1

HCID 178492824HCID 178492824, VerbindungAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To the 1 ml DMF solution of 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-4-oxo-3,4-dihydro-quinazoline-6-carbonitrile (10.0 mg, 0.02 mmol) was added sodium azide (16.7 mg, 0.24 mmol) and ammonium chloride (12.8 mg, 0.24 mmol). The reaction test tube was flushed with N2 and was irradiated at 200° C. for 40 minutes in the SmithSynthesizer Microwave Reactor with vigorous agitation by a magnetic stirrer. The mixture was cooled to room temperature, the solvent was removed by reduce pressure and extracted with water and ethyl acetate, dried over anhydrous MgSO4, and concentrated by rotary evaporation. Purification was accomplished by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase). The product was collected and dried under reduced pressure to give 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-6-(1H-tetrazol-5-yl)-3H-quinazolin-4-one (Yield 3.09 mg, 9.8%). 1H NMR (400 MHz, MeOD-d4): δ 1.79 (d, 3H, J=6.57 Hz), 3.39-3.12 (m, 8H), 3.70 (s, 3H), 3.92 (s, 3H), 4.70 (s, br, 1H), 7.17 (d, 2H, J=9.09 Hz), 7.76 (d, 2H, J=9.09 Hz), 7.87 (d, 1H, J=8.59 Hz), 8.47 (dd, 1H, J=8.59, 1.77 Hz), 8.89 (d, 1H, J=1.77 Hz). MS m/z calc. 510.18 found (ESI); 511.4 (M+1)+. Retention time 2.2 minutes.

Aufarbeitung

  1. customThe reaction test tube was flushed with N2
  2. customwas irradiated at 200° C. for 40 minutes in the SmithSynthesizer Microwave Reactor with vigorous agitation by a magnetic stirrer
  3. customthe solvent was removed
  4. extractionextracted with water and ethyl acetate
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. customPurification
  8. customThe product was collected
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ee664f6985c34da5bfbeddca3e721643
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642609B2

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