Sodium Hydroxide → 3-(3-{3-[4-(4-Biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid

HRID 410364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410364
C([O:3][C:4](=[O:51])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:36][CH2:35][N:34]([CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=5[C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[CH2:33][CH2:32]4)=[CH:27][CH:26]=3)[C:16]2=[NH:50])[CH:6]=1)C.[OH-].[Na+]>CO>[C:39]1([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[CH2:37][N:34]1[CH2:33][CH2:32][N:31]([C:28]2[CH:27]=[CH:26][C:25]([CH2:24][N:17]3[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:15]([CH2:14][CH2:13][CH2:12][O:11][C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:4]([OH:51])=[O:3])[C:16]3=[NH:50])=[CH:30][CH:29]=2)[CH2:36][CH2:35]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 585649503-(3-{3-[4-(4-Biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid ethyl ester

Produkt 1

HCID 462411073-(3-{3-[4-(4-Biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acidAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-(3-{3-[4-(4-biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid ethyl ester (20 mg, 0.03 mmol) in MeOH (2 ml) at rt was added 1M NaOH (2 ml). The reaction was heated at to 80° C. for 5 h and then concentrated under reduced pressure. The material that remained was partitioned between EtOAc and H2O and the organic layer was separated, dried (Na2SO4), filtered and concentrated under reduced pressure to give 3-(3-{3-[4-(4-biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid (10 mg, 52%). HPLC-MS [M+1]+ 327. 1H NMR (500 MHz, CHLOROFORM-d) □ ppm 2.13 (2 H, br s), 2.36 (4 H, br s), 2.87 (4 H, br. s.), 3.39 (2 H, s), 3.99 (2 H, br s), 4.39 (2 H, br s), 5.24-5.55 (2 H, m), 6.37-6.87 (3 H, m), 7.09 (7 H, br s), 7.29-7.67 (11 H, m).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe material that remained was partitioned between EtOAc and H2O
  3. customthe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3d1f1da8796c414ca7f83ebcf5380348
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759520B2

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