Hydrochloric Acid → HCID 24957323, compound

HRID 1097789Notes

Reaction equation

HRID 1097789 reaction equation
[N:1]1([CH:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8](=O)[C:7]2([CH3:18])[CH3:17])[CH:5]=[CH:4][N:3]=[CH:2]1.B.C1COCC1.Cl.[H][H].[OH-].[Na+]>C1COCC1>[N:1]1([CH:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8][C:7]2([CH3:18])[CH3:17])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 24957321HCID 24957321, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24957323HCID 24957323, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-imidazol-1-yl-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one (80 mg, 0.332 mmol) in THF (3 mL) at room temperature is added BH3-THF (3.3 mL, 1.0 M solution) and the mixture is stirred at room temperature for 1 h. To the reaction mixture is added 6N HCl until no hydrogen gas evolves from the solution. The reaction mixture is stirred for 2 h at room temperature and is added aqueous 10% NaOH to adjust PH=12 and then the mixture is extracted into CH2Cl2 and washed by brine; dried with anhydrous sodium sulfate and concentrated to give the crude compound. Reverse phase HPLC (CH3CN:H2O=20 to 90% over 20 mins) purification gives the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.85 (s, 3 H), 1.06 (s, 3 H), 2.92-3.00 (m, 1 H), 3.12 (d, J=11.9 Hz, 1 H), 4.18 (br. s., 1 H), 4.78 (s, 1 H), 6.57-6.66 (m, 2 H), 6.80 (s, 1 H), 6.86 (d, J=7.1 Hz, 1 H), 7.02 (s, 1 H), 7.07-7.14 (m, 1 H), 7.47 (s, 1 H).

Workup

  1. stirringThe reaction mixture is stirred for 2 h at room temperature
  2. extractionthe mixture is extracted into CH2Cl2
  3. washwashed by brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give the crude compound
  7. customphase HPLC (CH3CN:H2O=20 to 90% over 20 mins) purification

Sources & evidence

ORD record
ord-023ad0abab7647fba736cdf13d3f1fac
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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