Hydrochloric Acid → HCID 46941191, compound

HRID 2410610Notes

Reaction equation

HRID 2410610 reaction equation
Cl[C:2]1[CH:18]=[C:17]([C:19]2[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])=[C:26]([CH2:37][O:38][CH3:39])[CH:25]=3)[O:21][N:20]=2)[CH:16]=[CH:15][C:3]=1[CH2:4][N:5]([CH3:14])[CH2:6][C:7]([O:9]C(C)(C)C)=[O:8].[ClH:40]>O1CCOCC1>[CH3:39][O:38][CH2:37][C:26]1[CH:25]=[C:24]([C:22]2[O:21][N:20]=[C:19]([C:17]3[CH:16]=[CH:15][C:3]([CH2:4][N:5]([CH3:14])[CH2:6][C:7]([OH:9])=[O:8])=[CH:2][C:18]=3[Cl:40])[N:23]=2)[CH:29]=[CH:28][C:27]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66677471HCID 66677471, compound

Product 1

HCID 46941191HCID 46941191, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To tert-butyl 2-((2-chloro-4-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)(methyl)amino)acetate (0.192 g, 0.35 mmol) was added a 4N solution of HCl in dioxane (2 mL) and the reaction mixture stirred at 80° C. for 2 hours. The reaction mixture was allowed to cool and the solvent evaporated in vacuo. The residue was purified by SCX-2 chromatography eluting with methanol followed by DCM and ammoniacal MeOH (7M) to afford the title compound as a colorless gum. 1H NMR (CDCl3, 400 MHz) δ 8.38 (1H, s), 8.12 (1H, d, J=7.9 Hz), 8.07 (1H, d, J=8.0 Hz), 7.72 (1H, s), 7.55 (1H, d, J=8.1 Hz), 7.32-7.19 (4H, m), 7.10 (1H, d, J=7.4 Hz), 4.19 (4H, m), 3.57 (2H, s), 3.28 (3H, s), 2.72 (3H, s), 2.05 (3H, s). LC/MS (Method A): 492 (M+H)+. HPLC (Method F) Rt 3.19 min (Purity: 98.8%).

Workup

  1. temperatureto cool
  2. customthe solvent evaporated in vacuo
  3. customThe residue was purified by SCX-2 chromatography
  4. washeluting with methanol

Sources & evidence

ORD record
ord-b79b9672a97e42bfac713b901e44024a
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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