Pyridine → HCID 67174405, compound

HRID 1256164Notes

Reaction equation

HRID 1256164 reaction equation
[CH3:1][C:2]1[N:3]=[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])[O:5][CH:6]=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[O:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655234HCID 86655234, compound

Product 1

HCID 67174405HCID 67174405, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-((4-methyloxazol-2-yl)methyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (180 mg, 0.47 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (106 mg, 0.71 mmol) in 10 mL of ACN was added pyridine (114 uL, 1.41 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 (236 mg, yield 94%). 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. 2,2,2-Trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((4-methyloxazol-2-yl)methyl)phenyl)acetamide MS calcd for (C20H17BN3O6F3S): 495.2. MS found (ESI negative): (M−H)−=494.1. 1H NMR (DMSO-d6) δ (ppm): 11.51 (s, 1H), 10.43 (s, 1H), 9.20 (s, 1H), 7.91 (d, J=8.8 Hz, 1H), 7.77 (s, J=8.8 Hz, 1H), 7.69 (s, 1H), 7.53 (s, 1H), 7.44 (s, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 4.86 (s, 2H), 4.47 (s, 2H), 2.01 (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-7d48654772324ab4ab0288784f9177ae
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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