Pyridine → HCID 67174085, compound

HRID 1256169Notes

Reaction equation

HRID 1256169 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([CH2:8][C:9]2[CH:14]=[C:13]([NH:15]C(=O)C(F)(F)F)[CH:12]=[CH:11][C:10]=2[S:22](Cl)(=[O:24])=[O:23])=[N:5][N:4]=1)[CH3:2].[NH2:26][C:27]1[CH:28]=[CH:29][C:30]2[CH2:34][O:33][B:32]([OH:35])[C:31]=2[CH:36]=1.N1C=CC=CC=1>C(#N)C>[NH2:15][C:13]1[CH:12]=[CH:11][C:10]([S:22]([NH:26][C:27]2[CH:28]=[CH:29][C:30]3[CH2:34][O:33][B:32]([OH:35])[C:31]=3[CH:36]=2)(=[O:23])=[O:24])=[C:9]([CH2:8][C:6]2[O:7][C:3]([CH2:1][CH3:2])=[N:4][N:5]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655239HCID 86655239, compound

Product 1

HCID 67174085HCID 67174085, compoundYield 112.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-((5-ethyl-1,3,4-oxadiazol-2-yl)methyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (335 mg, 0.84 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (125 mg, 0.84 mmol) in 5 mL of ACN was added pyridine (205 uL, 2.53 mmol) dropwise. The reaction mixture was stirred at room temperature for 3 hours. After the mixture was concentrated, the residue was extracted with ethyl acetate and washed with water, 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated to give the desired compound as a yellow solid (390 mg, yield 91%).

Workup

  1. concentrationAfter the mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washwashed with water, 1N HCl and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c7c74d452034aaf98893607cdee9868
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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