Hydrochloric Acid → HCID 56601367, compound

HRID 572592Notes

Reaction equation

HRID 572592 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([N:33]([CH3:42])[CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:28])=[C:18]([C:29]([F:32])([F:31])[F:30])[CH:17]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1.Cl>O1CCOCC1>[CH3:1][O:2][CH2:3][CH:4]([N:33]([CH3:42])[CH2:34][C:35]([OH:37])=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:28])=[C:18]([C:29]([F:32])([F:31])[F:30])[CH:17]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66652678HCID 66652678, compound

Product 1

HCID 56601367HCID 56601367, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To tert-butyl N-[2-methoxy-1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-N-methylglycinate (0.078 g; 0.13 mmol) was added HCl solution in dioxane (4 M; 4 mL) and the reaction mixture stirred at ambient temperature for 18 hours and at 80° C. for 2 hour. The reaction mixture was allowed to cool and the solvent evaporated in vacuo. The residue was triturated with ether and dried under vacuum. The solid was dissolved in DMSO-d6 and evaporated to afford the title compound as a colourless gum (0.055 g, 75%). 1H NMR: (DMSO-d6/D2O, 400 MHz) δ 8.57 (1H, s), 8.54-8.52 (1H, d, J=8 Hz), 8.24 (2H, d, J=8 Hz), 7.79 (2H, d, J=8 Hz), 7.69 (1H, d, J=8 Hz), 7.40-7.37 (2H, m), 7.33-7.31 (1H, m), 7.19 (1H, d, J=7.2 Hz), 4.78 (1H, m), 4.13-4.10 (1H, m), 3.97 (1H, m), 3.87-3.83 (2H, m), 3.36 (3H, s), 2.75 (3H, s), 2.03 (3H, s). LC/MS (Method B): 526 (M+H)+. HPLC (Method C) Rt 9.13 min (Purity: 98.2%).

Workup

  1. temperatureto cool
  2. customthe solvent evaporated in vacuo
  3. customThe residue was triturated with ether
  4. customdried under vacuum
  5. dissolutionThe solid was dissolved in DMSO-d6
  6. customevaporated

Sources & evidence

ORD record
ord-5965fdaaa33c47e3b11115423c8a051f
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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