Pyridine → HCID 67174980, compound

HRID 1256151Notes

Reaction equation

HRID 1256151 reaction equation
[CH2:1]([S:4]([CH2:7][C:8]1[CH:13]=[C:12]([NH:14]C(=O)C(F)(F)F)[CH:11]=[CH:10][C:9]=1[S:21](Cl)(=[O:23])=[O:22])(=[O:6])=[O:5])[CH2:2][CH3:3].[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][S:4]([CH2:1][CH2:2][CH3:3])(=[O:5])=[O:6])[CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655223HCID 86655223, compound

Product 1

HCID 67174980HCID 67174980, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-(propylsulfonylmethyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (700 mg, 1.7 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (384 mg, 2.58 mmol) in 10 mL of ACN was added pyridine (278 uL, 3.4 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. A solution of this crude compound in 7M ammonium in MeOH (10 mL) was stirred in a sealed tube at 50° C. for 4 hours. After concentrated, the crude mixture was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the title compound as an off-white solid (428 mg, yield 59%). MS calcd for (C17H21BN2O6S2): 424.3. MS found (ESI negative): (M−H)−=423.1. 1H NMR (DMSO-d6) δ (ppm): 9.88 (s, 1H), 9.20 (bs, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.41 (s, 1H), 7.21 (d, J=8.4 Hz, 1H), 7.08 (d, J=8.0 Hz, 1H), 6.73 (s, 1H), 6.47 (d, J=8.4 Hz, 1H), 4.86 (s, 2H), 4.69 (s, 2H), 2.97 (t, 2H), 1.61 (m, 2H), 0.89 (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
  6. stirringA solution of this crude compound in 7M ammonium in MeOH (10 mL) was stirred in a sealed tube at 50° C. for 4 hours
  7. concentrationAfter concentrated
  8. customthe crude mixture was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-43da186de83f46fe92bbc4c94589abfe
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

Loading…