Hydrochloric Acid → (3-((3-(4-(2,2-Dimethoxyethyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)-(phenyl)methanamine

HRID 332698Notes

Reaction equation

HRID 332698 reaction equation
Cl.O1CCOCC1.C(OC(=O)[NH:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]2[O:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41][CH:42]4[O:46][CH2:45][CH2:44][O:43]4)=[CH:37][CH:36]=3)[N:31]=2)[CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C)(C)C>CO>[CH3:45][O:46][CH:42]([O:43][CH3:44])[CH2:41][C:38]1[CH:37]=[CH:36][C:35]([C:32]2[N:31]=[C:30]([CH2:29][O:28][C:24]3[CH:23]=[C:22]([CH:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH2:14])[CH:27]=[CH:26][CH:25]=3)[O:34][N:33]=2)=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71113095Tert-butyl((3-((3-(4-((1,3-dioxolan-2-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate

Product 1

HCID 86676912(3-((3-(4-(2,2-Dimethoxyethyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)-(phenyl)methanamineYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen chloride in dioxan (4.0 M, 5 mL, 24 mmol) was added to a solution of tert-butyl((3-((3-(4-((1,3-dioxolan-2-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate (1.01 g, 1.85 mmol) in methanol (5 mL), and the resultant solution was stirred at ambient temperature for 2 hours. The solvent was evaporated at reduced pressure, and the residue was loaded onto an SCX-2 cartridge. The cartridge was eluted with methanol (eight column volumes) followed by ammonia/methanol. Fractions containing the product were combined and evaporated at reduced pressure to afford the title compound (0.796 g, 96%).

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. washThe cartridge was eluted with methanol (eight column volumes)
  3. additionFractions containing the product
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-ac8db9a0604949fa8d40691f565cb010
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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