Triethylamine → HCID 72817086, compound

HRID 2110553Notes

Reaction equation

HRID 2110553 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[CH:10]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:11][CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O.[CH2:30]([N:37]1[CH2:42][CH:41]2[CH:39](N2N)[CH2:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[CH2:44]([N:46](CC)CC)C>C(#N)C>[CH2:30]([N:37]1[CH2:42][CH:41]2[CH:39]([CH:44]2[NH:46][CH2:12][CH2:11][CH:10]([C:4]2[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111657773-(2-Methoxy-5-methylphenyl)-3-phenylpropyl 4-methylbenzenesulfonateHCID 86609626HCID 86609626, compound

Product 1

HCID 72817086HCID 72817086, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The compound, toluene-4-sulphonic acid-3-(2-methoxy-5-methylphenyl)-3-phenylpropyl ester (prepared as described in EP 0325571, 1.5 gm, 3.66 mmole, 1 eq) was dissolved in dry acetonitrile (4 ml). To the reaction mixture, 3-benzyl-3,6-diazabicyclo[3.1.0]hex-6-yl amine, 1.38 gm, 7.32 mmole, 2 eq, (prepared according to T. F. Braish et al. Synlett 1996, 1100) and triethylamine (5.1 ml) were added. The resulting reaction mixture was heated at 80° C. for 4 days. The solvents were evaporated off, from the reaction mixture under reduced pressure. The residue was dissolved in ethyl acetate, and washed with saturated sodium bicarbonate solution. The organic layer was separated, dried over sodium sulphate and concentrated under high vaccum. The crude compound was purified through column chromatography using ethyl acetate in hexane solvent system.

Workup

  1. additionwere added
  2. customThe resulting reaction mixture
  3. customThe solvents were evaporated off, from the reaction mixture under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate solution
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under high vaccum
  9. customThe crude compound was purified through column chromatography

Sources & evidence

ORD record
ord-157eeb337b9848b986344c31861f6bea
Source dataset
uspto-grants-2009_04
Patent number
US07517905B2

Reaction notes

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