Hydrochloric Acid → HCID 178489115, compound

HRID 1360782Notes

Reaction equation

HRID 1360782 reaction equation
C[O:2][C:3](=[O:38])[C:4]([CH3:37])([CH3:36])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]4[O:23][C:24]([C:27]5[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=5)=[N:25][N:26]=4)=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:35])[CH:7]=1.[OH-].[Na+].Cl>CO>[CH3:34][O:33][C:30]1[CH:29]=[CH:28][C:27]([C:24]2[O:23][C:22]([C:20]3[CH:19]=[CH:18][C:16]4[NH:17][C:13]([C:9]5[C:8]([CH3:35])=[CH:7][C:6]([CH2:5][C:4]([CH3:36])([CH3:37])[C:3]([OH:38])=[O:2])=[CH:11][C:10]=5[CH3:12])=[N:14][C:15]=4[CH:21]=3)=[N:26][N:25]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178500174HCID 178500174, compound

Product 1

HCID 178489115HCID 178489115, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(4-{5-[5-(4-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester (340 mg, 0.667 mmol) and aqueous 1M NaOH (5 mL, 5 mmol) in MeOH (5 mL) was stirred at room temperature for 18 h and then heated at 50° C. for 1 h. After the mixture was cooled to room temperature, the mixture was slowly acidified to pH 2˜3 by addition of 3M HCl. The product precipitated and was separated from the solution. The solid was dissolved in a small quantity of DMSO and purified by HPLC (basic) to give the title compound as a solid. 1H NMR (CD3OD, 400 MHz) δ ppm 8.55-8.45 (m, 1H), 8.23 (d, J=8 Hz, 2H), 8.22 (d, J=8 Hz, 1H), 7.95-7.85 (m, 1H), 7.26 (d, J=8 Hz, 2H), 7.15 (s, 2H), 4.02 (s, 3H), 2.99 (s, 2H), 2.26 (s, 6H), 1.30 (s, 6H). m/z 497.2 (MH+).

Workup

  1. temperatureheated at 50° C. for 1 h
  2. temperatureAfter the mixture was cooled to room temperature
  3. customThe product precipitated
  4. customwas separated from the solution
  5. dissolutionThe solid was dissolved in a small quantity of DMSO
  6. custompurified by HPLC (basic)

Sources & evidence

ORD record
ord-a00d9a8592f94937a4141bc1be49bd5e
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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