Hydrochloric Acid → HCID 178467816, compound

HRID 2368159Notes

Reaction equation

HRID 2368159 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH3:12])[CH2:5]P(=O)(OC)OC.[CH:13]1([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]3[C:25]([CH:26]=2)=[N:24][N:23]([C@H:27]2[CH2:32][CH2:31][C@H:30]([CH:33]=O)[CH2:29][CH2:28]2)[CH:22]=3)[CH2:15][CH2:14]1.Cl>COCCOC>[CH:13]1([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]3[C:25]([CH:26]=2)=[N:24][N:23]([C@H:27]2[CH2:32][CH2:31][C@H:30](/[CH:33]=[CH:5]/[C:4](=[O:3])[CH3:12])[CH2:29][CH2:28]2)[CH:22]=3)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 178520961HCID 178520961, compound

Product 1

HCID 178467816HCID 178467816, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Sodium hydride (0.292 g) was added to a solution of dimethyl 2-oxopropylphosphonate (2.021 g) in 1,2-dimethoxyethane (50 mL) under ice-cooling in small portions. The reaction mixture was stirred for 1 hr under ice-cooling, and a solution of trans-4-[6-(cyclopropylmethoxy)-2H-indazol-2-yl]cyclohexanecarbaldehyde (3.30 g) in 1,2-dimethoxyethane (50 mL) was added under ice-cooling. The reaction mixture was stirred at room temperature for 3 hr, poured into 1N hydrochloric acid under ice-cooling and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (2.85 g).

Workup

  1. temperaturecooling in small portions
  2. temperaturecooling
  3. temperaturecooling
  4. stirringThe reaction mixture was stirred at room temperature for 3 hr
  5. temperaturecooling
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-48c116501d604c2693f2ef56c867cfe9
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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