Ammonia → 1-Amino-3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol

HRID 1094302Notes

Reaction equation

HRID 1094302 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:14]2[N:18]=[C:17]([C:19]3[S:20][C:21]([CH2:24][CH3:25])=[CH:22][CH:23]=3)[O:16][N:15]=2)[CH:5]=[C:6]([CH3:13])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][O:11]1.[NH3:26]>CO>[NH2:26][CH2:12][CH:10]([OH:11])[CH2:9][O:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([C:14]2[N:18]=[C:17]([C:19]3[S:20][C:21]([CH2:24][CH3:25])=[CH:22][CH:23]=3)[O:16][N:15]=2)=[CH:5][C:6]=1[CH3:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 866393493-(3,5-Dimethyl-4-oxiranylmethoxy-phenyl)-5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazole

Product 1

HCID 666369791-Amino-3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazole (123 mg, 0.345 mmol) in 7 N NH3 in methanol (10 mL) is stirred at 45° C. for 16 h. The solvent is evaporated and the residue is separated by chromatography on prep. TLC plates with DCM containing 6% of 7 N NH3 in methanol to give 1-amino-3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (35 mg) as a white solid; LC-MS: tR=0.84 min, [M+1]+=374.14.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is separated by chromatography on prep

Sources & evidence

ORD record
ord-f1a4c0bab375493c83c8e599ce91c6dd
Source dataset
uspto-grants-2012_03
Patent number
US08133910B2

Reaction notes

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