Hydrochloric Acid → HCID 71767641, compound

HRID 1771436Notes

Reaction equation

HRID 1771436 reaction equation
[CH2:1]([CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:13]C2CCCCO2)[CH:5]([C:20]2[NH:21][CH2:22][CH2:23][N:24]=2)[O:4]1)[CH3:2].[ClH:25]>CO.C(OCC)C>[ClH:25].[NH:24]1[CH2:23][CH2:22][N:21]=[C:20]1[CH:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([OH:13])[C:11]=2[CH2:12][CH:3]([CH2:1][CH3:2])[O:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 117925450HCID 117925450, compound

Product 1

HCID 71767641HCID 71767641, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Methyl 3-ethyl-5-hydroxyisochroman-1-carboxylate (90 mg) was dissolved dichloromethane (1 mL) and 3,4-dihydro-2H-pyran (52 μL) and pyridinium p-toluenesulfonate (9.6 mg) were added. After 28 hours more 3,4-dihydro-2H-pyran (102 μL) and pyridinium p-toluenesulfonate (10 mg) were added and mixture was stirred for another 24 hours. 3,4-Dihydro-2H-pyran (200 μL) was then added and mixture was stirred overnight after which it was diluted with diethyl ether (5 ml) and washed with saturated NaHCO3-solution. Organic phase was dried with Na2SO4 and concentrated. Purification of the evaporation residue by column chromatography (ethyl acetate-heptane) afforded 37 mg of oil that was converted to 2-(3-ethyl-5-((tetrahydro-2H-pyran-2-yl)oxy)isochroman-1-yl)-4,5-dihydro-1H-imidazole (13 mg) using the synthesis method A3. The crude product of this procedure was dissolved in methanol (1 ml) and HCl solution in diethyl ether (2M, 39 μL) was added. After 2.5 hours reaction mixture was concentrated and the residue was taken in water (10 mL). The solution was washed with ethyl acetate and the water layer was concentrated in freeze dryer to afford the title compound. (Yield 6 mg).

Workup

  1. customthe synthesis method A3
  2. customAfter 2.5 hours reaction mixture
  3. concentrationwas concentrated
  4. washThe solution was washed with ethyl acetate
  5. concentrationthe water layer was concentrated in freeze dryer

Sources & evidence

ORD record
ord-02f8fd03327c4f4ebb262ef58fa48581
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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