Pyridine → HCID 67312003, compound

HRID 1256171Notes

Reaction equation

HRID 1256171 reaction equation
[CH2:1]([C:4]1[O:8][C:7]([CH2:9][C:10]2[CH:15]=[C:14]([NH:16]C(=O)C(F)(F)F)[CH:13]=[CH:12][C:11]=2[S:23](Cl)(=[O:25])=[O:24])=[N:6][N:5]=1)[CH2:2][CH3:3].[NH2:27][C:28]1[CH:29]=[CH:30][C:31]2[CH2:35][O:34][B:33]([OH:36])[C:32]=2[CH:37]=1.N1C=CC=CC=1>C(#N)C>[NH2:16][C:14]1[CH:13]=[CH:12][C:11]([S:23]([NH:27][C:28]2[CH:29]=[CH:30][C:31]3[CH2:35][O:34][B:33]([OH:36])[C:32]=3[CH:37]=2)(=[O:24])=[O:25])=[C:10]([CH2:9][C:7]2[O:8][C:4]([CH2:1][CH2:2][CH3:3])=[N:5][N:6]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655241HCID 86655241, compound

Product 1

HCID 67312003HCID 67312003, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-((5-propyl-1,3,4-oxadiazol-2-yl)methyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (430 mg, 1.05 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (234 mg, 1.57 mmol) in 5 mL of ACN was added pyridine (253 uL, 3.13 mmol) dropwise. The reaction mixture was stirred at room temperature for 16 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 (410 mg, yield 75%).

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-1fd6c2dbfae540d5a93b377c9302f0bd
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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