Hydrochloric Acid → 3-(3,5-Dichloro-4-{6-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-phenyl)-propionic acid

HRID 1360798Notes

Reaction equation

HRID 1360798 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([C:16]2[NH:20][C:19]3[CH:21]=[C:22]([C:25]4[O:26][C:27]([C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=5)=[N:28][N:29]=4)[CH:23]=[CH:24][C:18]=3[N:17]=2)=[C:11]([Cl:37])[CH:10]=1)(C)(C)C.Cl>C1(OC)C=CC=CC=1.O1CCOCC1>[Cl:15][C:13]1[CH:14]=[C:9]([CH2:8][CH2:7][C:6]([OH:38])=[O:5])[CH:10]=[C:11]([Cl:37])[C:12]=1[C:16]1[NH:20][C:19]2[CH:21]=[C:22]([C:25]3[O:26][C:27]([C:30]4[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=4)=[N:28][N:29]=3)[CH:23]=[CH:24][C:18]=2[N:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 669665013-(3,5-Dichloro-4-{6-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 252354603-(3,5-Dichloro-4-{6-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-phenyl)-propionic acid

Reagents, catalysts & solvents 2

HCID 7519AnisoleCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a 100 ml rbf was added 0.090 g (0.157 mmol) of 3-(3,5-Dichloro-4-{6-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-phenyl)-propionic acid tert-butyl ester, a few drops of anisole, and 3 mL 4M HCl in 1,4-dioxane. The purple solution was allowed to stir at r.t. for 72 h. The reaction mixture was concentrated and the residue purified by basic HPLC (ACN/0.005 mM H2O—NH4OH, 2.5:7.5 to 8:2) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.78 (t, J=7.45 Hz, 2H) 3.07 (t, J=7.33 Hz, 2H) 7.75 (s, 2H) 7.84-7.89 (m, 2H) 7.99 (d, J=7.45 Hz, 1H) 8.20 (dd, J=8.46, 1.39 Hz, 1H) 8.32-8.37 (m, 2H) 8.56 (br. s., 1H). MS (m/z) 515.0 M (+1), tR=1.19, Meth 10

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by basic HPLC (ACN/0.005 mM H2O—NH4OH, 2.5:7.5 to 8:2)

Sources & evidence

ORD record
ord-7e003b81cc1e443b8c53dcf37cb0465a
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

Loading…