StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium Bicarbonate → Tert-butyl 4-(((4-methyl-5-phenyl-4h-1,2,4-triazol-3-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)butylcarbamate

HRID 2196627
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2196627
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:4]=[C:3]1[CH:13]=O.[N:15]1[C:24]2[CH:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:22][CH2:21][CH2:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.CC(O)=O>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:5][N:4]=[C:3]1[CH2:13][N:25]([CH:23]1[C:24]2[N:15]=[CH:16][CH:17]=[CH:18][C:19]=2[CH2:20][CH2:21][CH2:22]1)[CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 115428934-methyl-5-phenyl-4H-1,2,4-triazole-3-carbaldehydeHCID 42609132558446-23-4

Produkt 1

HCID 59176412Tert-butyl 4-(((4-methyl-5-phenyl-4h-1,2,4-triazol-3-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)butylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 176Acetic AcidKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 4-methyl-5-phenyl-4H-1,2,4-triazole-3-carbaldehyde, 36, (0.41 g, 2.20 mmol) in 1,2-dichloroethane (4 mL) was added tert-butyl 4-(5,6,7,8-tetrahydroquinolin-8-ylamino)butylcarbamate, 3, (0.76 g, 2.40 mmol), sodium triacetoxyborohydride (0.84 g, 3.95 mmol), and AcOH (10 drops). The reaction mixture was heated to 65° C. and stirred for 18 h. The reaction mixture was cooled to room temperature and poured into saturated aqueous NaHCO3 (15 mL) and extracted with ethyl acetate (2×10 mL). The combined organic phases were washed with brine then dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-5% methanol/dichloromethane) to yield 37: 1H NMR (400 MHz, CDCl3) δ 8.40, (d, J=5.2 Hz, 1H), 7.60-7.57 (m, 2H), 7.48-7.44, (m, 3H), 7.31, (d, J=7.2 Hz, 1H), 7.0, (dd, J=8.0, 5.2 Hz, 1H), 5.01, (bs, 1H), 4.20-3.92, (m, 3H), 3.20-2.60, (m, 6H), 2.20-1.85, (m, 4H), 1.75-1.30 (m, 13H); ESI+ MS: m/z (rel intensity) 491 (100, M+H). Step g: Preparation of N-(4-aminobutyl)-N-((4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)methyl)-5,6,7,8-tetrahydroquinolin-8-amine tetrahydrochloride (BQ). Through a methanol (2 mL) solution of 37 (0.16 g, 0.32 mmol) was bubbled HCl(g) generated by the addition of sulfuric acid to dry NaCl. Upon total conversion of the reaction as monitored by LC-MS, the reaction mixture was concentrated in vacuo to yield BQ: ESI+ MS: m/z (rel intensity) 391 (100, M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by silica gel chromatography (0-5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-1a39b64072d4455eb5ada83c89e9c672
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08338448B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion