Hydrochloric Acid → HCID 66965603, compound

HRID 1515006Notes

Reaction equation

HRID 1515006 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:37]=[CH:36][C:15]3[N:16]=[C:17]([C:19]4[C:24]([CH3:25])=[CH:23][C:22]([O:26][CH2:27][C@@H:28]5[CH2:32][O:31]C(C)(C)[O:29]5)=[CH:21][C:20]=4[CH3:35])[NH:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].Cl.[OH-].[Na+].O>CO.CCOC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:37]=[CH:36][C:15]3[N:16]=[C:17]([C:19]4[C:20]([CH3:35])=[CH:21][C:22]([O:26][CH2:27][C@@H:28]([OH:29])[CH2:32][OH:31])=[CH:23][C:24]=4[CH3:25])[NH:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66965569HCID 66965569, compound

Product 1

HCID 66965603HCID 66965603, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2,6-dimethylphenyl]-3H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide (120 mg, 0.24 mmol) in MeOH (3 mL) was added 1N HCl (3 mL) and the solution was stirred at ambient temperature for 3 h. The solution was basified to pH 10 with 1N NaOH and the mixture was partioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the organic layer was washed with water, brine, dried with MgSO4, filtered and concentrated. Purification by HPLC gave the title compound as a white solid. 1H NMR (Methanol-d4, 400 MHz): δ 8.22 (s, 1H), 7.90 (dd, 1H), 7.70 (d, 1H), 7.47 (s, 1H), 7.44 (dd, 1H), 7.13 (d, 1H), 6.80 (s, 2H), 4.11 (m, 1H), 4.03 (m, 2H), 3.72 (m, 2H), 2.29 (s, 3H), 2.26 (s, 3H), 2.14 (s, 6H). MS (m/z) 460.1 (M+1); Retention time: 1.23 min (Method 10).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by HPLC

Sources & evidence

ORD record
ord-9c8cf523923e4a1a9ece35eff798e078
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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