1,2-Dichloroethane → 5-isobutyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazol-2-amine

HRID 881743Notes

Reaction equation

HRID 881743 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.C(N1C=CC=CC1=O)(N1C=CC=CC1=O)=S.[N-:33]=[C:34]=S.[CH3:36][CH:37]([CH3:43])[CH2:38][C:39]([NH:41]N)=[O:40].C(Cl)CCl>C(Cl)Cl>[CH2:38]([C:39]1[O:40][C:34]([NH:13][C:12]2[CH:14]=[CH:15][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)=[N:33][N:41]=1)[CH:37]([CH3:43])[CH3:36]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 322833-MethylbutanehydrazideHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 178418790HCID 178418790, compound

Product 1

HCID 867008455-isobutyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazol-2-amineYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (200 mg, 0.91 mmol) in methylene chloride (4.5 ml) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (212 mg, 0.91 mmol) and stirred at room temperature for 1 hour. Upon complete formation of the isothiocyanate, 3-methylbutanehydrazide (159 mg, 1.37 mmol) was added to the mixture and stirred at room temperature for overnight. EDC (315 mg, 1.64 mmol) was then added and the reaction stirred at room temperature for 14 hours. The reaction was concentrated to dryness and taken up in water to form a slurry. The slurry was filtered and washed with water to afford the crude product, which was purified by column chromatography to afford the title compound as off-white solid after drying (217 mg, 69% yield). LC/MS, ESI-MS(+) m/z 344.1, RT 1.45 (Condition R).

Workup

  1. stirringstirred at room temperature for overnight
  2. stirringthe reaction stirred at room temperature for 14 hours
  3. concentrationThe reaction was concentrated to dryness
  4. customto form a slurry
  5. filtrationThe slurry was filtered
  6. washwashed with water
  7. customto afford the crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ed005af77e91469691fd62a286bd34c3
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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