Hydrochloric Acid → 2-phenyl-5-(pyrrolidin-1-yl)-1-(3,4,5-trimethoxybenzyl)-1H-benzo[d]imidazole

HRID 1888956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888956
[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH:21][CH2:22][C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)=[C:10]([NH:12][C:13](=O)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[OH-].N>C(O)C>[C:14]1([C:13]2[N:21]([CH2:22][C:23]3[CH:24]=[C:25]([O:33][CH3:34])[C:26]([O:31][CH3:32])=[C:27]([O:29][CH3:30])[CH:28]=3)[C:9]3[CH:8]=[CH:7][C:6]([N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)=[CH:11][C:10]=3[N:12]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 21862953Ammonia hydroxideHCID 68516839N-(5-(pyrrolidin-1-yl)-2-(3,4,5-trimethoxybenzylamino)phenyl)benzamide

Produkt 1

HCID 467007662-phenyl-5-(pyrrolidin-1-yl)-1-(3,4,5-trimethoxybenzyl)-1H-benzo[d]imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of N-(5-(pyrrolidin-1-yl)-2-(3,4,5-trimethoxybenzylamino)phenyl)benzamide in ethanol (20 mL) was added 4 N HCl. The reaction mixture was heated at 50° C. for 5 h, then cooled to room temperature. Excess acid was neutralized with ammonia hydroxide, and the resulting mixture was extracted with ethyl acetate (50 mL×3). The combined organics were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuum. The residue was subjected to flash chromatography on silica gel to obtain 2-phenyl-5-(pyrrolidin-1-yl)-1-(3,4,5-trimethoxybenzyl)-1H-benzo[d]imidazole as a solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.75-7.72 (m, 2H, 2′,6′-H), 7.55-7.50 (m, 3H, 3′, 4′, 5′-H), 7.34 (d, J=8 Hz, 1H, 7-H), 7.75 (d, J=2 Hz, 1H, 4-H), 6.60 (dd, J=8, 2 Hz, 1H, 6-H), 6.29 (s, 2H, 2″, 6″-H), 5.38 (s, 2H, CH2), 3.56 (s, 9H, OCH3), 3.25-3.22 (m, 4H, 2′,5′-H), 1.97-1.94 (m, 4H, 3′,4′-H); 13C NMR (100 MHz, DMSO-d6) δ (ppm): 152.9, 152.9, 152.5, 144.8, 144.0, 136.6, 132.7, 130.7, 129.4, 128.9, 128.9, 128.7, 128.7, 127.9, 111.1, 109.9, 103.7, 103.7, 99.9, 59.8, 55.7, 55.7, 47.9, 47.9, 47.7, 24.8, 24.8; EIMS: m/z 443 (M+).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate (50 mL×3)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f1c12e4a625f4f599753dce9f49c65f8
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501957B2

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