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Pyridine → 4-(2-Methyl-3-(4-methylbenzamido)phenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361349
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2361349
[NH2:1][C:2]1[C:3]([CH3:30])=[C:4]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([N:21]5[CH2:26][CH2:25][O:24][CH2:23][CH2:22]5)[CH:18]=4)[NH:13][C:12]=3[C:11]([C:27]([NH2:29])=[O:28])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1.N1C=CC=CC=1>ClCCl>[CH3:30][C:3]1[C:2]([NH:1][C:36](=[O:37])[C:35]2[CH:39]=[CH:40][C:32]([CH3:31])=[CH:33][CH:34]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[CH:18]=3)[NH:13][C:12]=2[C:11]([C:27]([NH2:29])=[O:28])=[N:10][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 134054-Methylbenzoyl ChlorideHCID 679946124-(3-Amino-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamide

Produkt 1

HCID 547667144-(2-Methyl-3-(4-methylbenzamido)phenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamideAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 4-(3-amino-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamide (0.0287 g, 0.071 mmol) and 4-methylbenzoyl chloride (0.013 g, 0.086 mmol) in dichloromethane (0.953 mL) under nitrogen was added pyridine (0.012 mL, 0.143 mmol). The vial was sealed and stirred at 40° C. After 15 min, the reaction was cooled to room temperature and concentrated in vacuo. It was diluted with MeOH (1 mL) and purified by reverse phase HPLC. The appropriate fractions were combined, basified with NaHCO3 (solid), and concentrated in vacuo. It was extracted with CH2Cl2 (3×). The organic layers were combined, dried over Na2SO4, and concentrated in vacuo to give the desired product (0.0192 g, 0.037 mmol, 51.7% yield) as a light yellow solid. LC/MS (M+H)=520.25; 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (s, 1H), 10.00 (s, 1H), 8.31 (d, J=2.2 Hz, 1H), 8.15 (s, 1H), 7.92 (s, 1H), 7.90 (s, 1H), 7.75 (d, J=2.0 Hz, 1H), 7.70 (d, J=8.80 Hz, 1H), 7.55 (d, J=7.0 Hz, 1H), 7.45 (t, J=7.7 Hz, 1H), 7.35 (s, 1H), 7.33 (s, 1H), 7.25-7.32 (m, 1H), 6.53 (d, J=2.2 Hz, 1H), 3.68 (m, 4H), 2.80-2.91 (m, 4H), 2.38 (s, 3H), 1.94 (s, 3H).

Aufarbeitung

  1. customThe vial was sealed
  2. temperaturethe reaction was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. additionIt was diluted with MeOH (1 mL)
  5. custompurified by reverse phase HPLC
  6. concentrationconcentrated in vacuo
  7. extractionIt was extracted with CH2Cl2 (3×)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-84de7d29f87e4b498998d2e5ac3a2a30
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08685969B2

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