Pyridine → HCID 67310994, compound

HRID 1256167Notes

Reaction equation

HRID 1256167 reaction equation
[CH3:1][C:2]1[O:6][C:5]([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:4][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:5]2[O:6][C:2]([CH3:1])=[N:3][N:4]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655237HCID 86655237, compound

Product 1

HCID 67310994HCID 67310994, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (300 mg, 0.78 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (194 mg, 1.3 mmol) in 5 mL of ACN was added pyridine (1.26 mL, 9.1 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 (318 mg, yield 82%). MS calcd for (C19H16BN4O6F3S): 496.2, MS found (ESI negative): (M−H)−=495.1. 1H NMR (DMSO-d6) δ (ppm): 11.5 (s, 1H), 10.5 (s, 1H), 9.20 (s, 1H), 7.93 (d, J=8.8 Hz, 1H), 7.80 (s, J=8.4 Hz, 1H), 7.59 (s, 1H), 7.44 (s, 1H), 7.25 (d, J=8.0 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 4.86 (s, 2H), 4.59 (s, 2H), 2.40 (s, 3H)

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-84303075e6984c1ba03b2b842fc52ca4
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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