Hydrochloric Acid → 3-(3-Chloro-4-isopropoxyphenyl)-5-(1,2,3,4-tetrahydroisoquinolin-5-yl)-1,2,4-oxadiazole

HRID 1172948Notes

Reaction equation

HRID 1172948 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH2:19][CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22]4)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH2:19][CH2:20][NH:21][CH2:22]4)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59556674tert-butyl 5-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 595566813-(3-Chloro-4-isopropoxyphenyl)-5-(1,2,3,4-tetrahydroisoquinolin-5-yl)-1,2,4-oxadiazoleYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 5-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.403 g, 0.858 mmol) in dioxane (17.15 ml) was added a 4N solution of HCl in dioxane (3.86 ml, 15.44 mmol). After about 15 h the reaction mixture was filtered. The resulting solid was partitioned between EtOAc and sat NaHCO3. The organic layer was separated, dried (MgSO4) filtered and concentrated in vacuo to provide 3-(3-chloro-4-isopropoxyphenyl)-5-(1,2,3,4-tetrahydroisoquinolin-5-yl)-1,2,4-oxadiazole (0.230 g, 73%) as a colorless solid. LCMS (Table 1, Method c) Rt=2.00 min, m/z 372 (M+H)+.

Workup

  1. filtrationAfter about 15 h the reaction mixture was filtered
  2. customThe resulting solid was partitioned between EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bbd22f43aa7450d8bb7e65a2593e1e3
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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