Pyridine → HCID 67173130, compound

HRID 1256163Notes

Reaction equation

HRID 1256163 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH:12]=[C:11]([NH:13]C(=O)C(F)(F)F)[CH:10]=[CH:9][C:8]=1[S:20](Cl)(=[O:22])=[O:21].[NH2:24][C:25]1[CH:26]=[CH:27][C:28]2[CH2:32][O:31][B:30]([OH:33])[C:29]=2[CH:34]=1.N1C=CC=CC=1>C(#N)C>[NH2:13][C:11]1[CH:10]=[CH:9][C:8]([S:20]([NH:24][C:25]2[CH:26]=[CH:27][C:28]3[CH2:32][O:31][B:30]([OH:33])[C:29]=3[CH:34]=2)(=[O:21])=[O:22])=[C:7]([CH2:6][C:2]2[O:1][CH:5]=[CH:4][N:3]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655233HCID 86655233, compound

Product 1

HCID 67173130HCID 67173130, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-(oxazol-2-ylmethyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (450 mg, 1.2 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (212 mg, 1.42 mmol) in 10 mL of ACN was added pyridine (228 uL, 2.8 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 (540 mg, yield 92%). 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-bdb0d4f4eb8546c6a0c758b60442e3a7
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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