Benzoxazole → HCID 131727470, compound

HRID 402133Notes

Reaction equation

HRID 402133 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[C:10]([OH:17])(=[O:16])/[CH:11]=[CH:12]\[C:13]([OH:15])=[O:14]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:11]1[C:12]2[C:13](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:2][N:3]([CH3:4])[CH2:10]1.[C:10]([OH:17])(=[O:16])/[CH:11]=[CH:12]\[C:13]([OH:15])=[O:14].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:11]1[C:12]2[C:13](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:2][N:3]([CH3:4])[CH2:10]1

Participants

5

Reactant 2

HCID 9228BenzoxazoleHCID 444266Maleic Acid

Product 2

HCID 11644658HCID 11644658, compoundHCID 131727470HCID 131727470, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Racemic 4-benzooxazol-2-yl-2-methyl-1,2,3,4-tetrahydroisoquinoline was prepared by a method similar to the one described in Example 132, starting from benzooxazole (Steps A to B). The free base (20 mg, 0.076 mmol) was dissolved in methanol (5 mL) was added a solution of maleic acid (8 mg, 0.076 mmol) in methanol (2 mL) at 0° C. The solution was stirred at room temperature for 12 h, concentrated, and the residue was slurried with diethyl ether. Filtration provided the as a 4-benzooxazol-2-yl-2-methyl-1,2,3,4-tetrahydroisoquinoline, maleate salt as a white powder (28 mg, 98%): 1H NMR (CD3OD, 500 MHz) δ 7.69 (dd, J=8.3, 6.8 Hz, 2H), 7.62 (dd, J=8.3, 1.3 Hz, 2H), 7.48-7.36 (m, 5H), 7.28 (d, J=2.9 Hz, 1H), 5.42 (s, 2H), 4.98-4.97 (m, 1H), 4.43-4.33 (m, 2H), 4.03 (s, 1H), 3.81-3.77 (m, 1H), 3.04 (s, 3H); ESI-MS m/z=265 [M+H]+; mp 135-140° C.; HPLC 97.5% AUC.

Workup

  1. concentrationconcentrated
  2. filtrationFiltration

Sources & evidence

ORD record
ord-582935143f694e3695bc2b8dba901e8e
Source dataset
uspto-grants-2014_06
Patent number
US08741901B2

Reaction notes

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