Diisopropylethylamine → HCID 67445706, compound

HRID 1666594Notes

Reaction equation

HRID 1666594 reaction equation
[CH:1]([O:4][C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[CH3:15])([CH3:3])[CH3:2].[CH2:16]([O:19][C:20]1[C:29]([CH3:30])=[CH:28][C:23]([C:24]([NH:26]O)=[NH:25])=[CH:22][C:21]=1[CH3:31])[CH:17]=[CH2:18].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl.CC(=O)OCC>[CH2:16]([O:19][C:20]1[C:29]([CH3:30])=[CH:28][C:23]([C:24]2[N:26]=[C:9]([C:8]3[CH:7]=[C:6]([CH3:15])[C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[C:13]([CH3:14])[CH:12]=3)[O:11][N:25]=2)=[CH:22][C:21]=1[CH3:31])[CH:17]=[CH2:18]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 28643161HCID 28643161, compoundHCID 178458380HCID 178458380, compound

Product 1

HCID 67445706HCID 67445706, compoundYield 111.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-isopropoxy-3,5-dimethyl-benzoic acid (175 mg, 794 μmol), 4-allyloxy-N-hydroxy-3,5-dimethyl-benzamidine (165 mg, 792 μmol) and DIPEA (128 mg, 993 μmol) in DCM (10 mL), TBTU (321 mg, 1.00 mmol) is added at 0° C. The mixture is stirred at 0° C. for 1 h, then at rt for 5 h, before it is diluted with EA (100 mL) and washed with sat. aq. NaHCO3 solution (2×30 mL). The org. extract is dried over Na2SO4, filtered and evaporated. The residue is dissolved in dioxane (10 mL) and stirred at 90° C. for 2 days. The solvent is evaporated and the residue is dried to give crude 3-(4-allyloxy-3,5-dimethyl-phenyl)-5-(4-isopropoxy-3,5-dimethyl-phenyl)-[1,2,4]oxadiazole (346 mg); LC-MS: tR=1.25 min, [M+1]+=393.47.

Workup

  1. additionis added at 0° C
  2. waitat rt for 5 h
  3. washwashed with sat. aq. NaHCO3 solution (2×30 mL)
  4. extractionextract
  5. dry with materialis dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue is dissolved in dioxane (10 mL)
  9. stirringstirred at 90° C. for 2 days
  10. customThe solvent is evaporated
  11. customthe residue is dried

Sources & evidence

ORD record
ord-044ab44a6afa4c75864441d1a0c517e7
Source dataset
uspto-grants-2011_10
Patent number
US08044076B2

Reaction notes

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