Pyridine → HCID 67174436, compound

HRID 1256173Notes

Reaction equation

HRID 1256173 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][C:8]2[CH:13]=[C:12]([NH:14]C(=O)C(F)(F)F)[CH:11]=[CH:10][C:9]=2[S:21](Cl)(=[O:23])=[O:22])[N:3]=1.[NH2:25][C:26]1[CH:27]=[CH:28][C:29]2[CH2:33][O:32][B:31]([OH:34])[C:30]=2[CH:35]=1.N1C=CC=CC=1>C(#N)C>[NH2:14][C:12]1[CH:11]=[CH:10][C:9]([S:21]([NH:25][C:26]2[CH:27]=[CH:28][C:29]3[CH2:33][O:32][B:31]([OH:34])[C:30]=3[CH:35]=2)(=[O:22])=[O:23])=[C:8]([CH2:7][C:4]2[N:3]=[C:2]([CH3:1])[O:6][N:5]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655243HCID 86655243, compound

Product 1

HCID 67174436HCID 67174436, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (490 mg, 1.3 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (627 mg, 4.21 mmol) in 10 mL of ACN was added pyridine (680 uL, 8.4 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 residue (555 mg, yield 88%). A small portion of the crude mixture was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the title compound as a yellow solid.

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-27c270ef52584ac8acbdc4e7c257d73b
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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