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Phosphorus oxychloride → 2-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carbonitrile

HRID 44515
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 44515
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[C:5]2[CH:18]=[C:19]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:20]=[C:21]([C:22]([NH2:24])=O)[C:4]=2[N:3]=1.O=P(Cl)(Cl)Cl>ClCCl.CN(C=O)C>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[C:5]2[CH:18]=[C:19]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:20]=[C:21]([C:22]#[N:24])[C:4]=2[N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 569598302-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carboxamide

Produkt 1

HCID 569596832-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carbonitrileAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To the mixture of 2-methyl-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazole-4-carboxamide, prepared as described in Example 33 (0.4 g, 0.999 mmol) in Dichloromethane (DCM) (50 mL) was added in POCl3 (0.931 mL, 9.99 mmol) and followed by the addition of ten drops of DMF. The reaction was stirred at rt for 1 h. The mixture was quenched with aqueous sodium bicarbonate solution. The aqueous phase was extracted with DCM (100 mL). The combined organic phase was washed with Brine then dried (MgSO4), filtered and the solvent removed in-vacuo. The crude was purified on silica (20˜50% EtOAc/Hexane) to give the product (0.246 g, 64%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.45 (s, 3H), 2.96-3.15 (m, 4H), 3.62-3.72 (m, 4H), 6.05 (s, 2H), 6.32 (d, J=7.07 Hz, 1H), 7.29-7.44 (m, 3H), 7.57-7.74 (m, 2H), 7.86 (d, J=8.08 Hz, 1H), 8.02 (d, J=7.83 Hz, 1H) 8.22 (d, 1H). MS (ES+) m/z 383.2 [M+H]+.

Aufarbeitung

  1. customprepared
  2. customThe mixture was quenched with aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted with DCM (100 mL)
  4. washThe combined organic phase was washed with Brine
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in-vacuo
  8. customThe crude was purified on silica (20˜50% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-06e3663ce94b464ba155a5f80b58f6be
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08541411B2

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