Hydrochloric Acid → N-(3-fluoro-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetamide

HRID 1256063Notes

Reaction equation

HRID 1256063 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[C:7]([F:15])[CH:6]=1)(=[O:3])[CH3:2].[NH2:16][C:17]1[CH:18]=[CH:19][C:20]2[CH2:24][O:23][B:22]([OH:25])[C:21]=2[CH:26]=1.C(N(CC)CC)C.Cl>CN(C)C=O>[F:15][C:7]1[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][C:8]=1[S:11](=[O:13])(=[O:12])[NH:16][C:17]1[CH:18]=[CH:19][C:20]2[CH2:24][O:23][B:22]([OH:25])[C:21]=2[CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 167710844-Acetamido-2-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 67174565N-(3-fluoro-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetamideYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-acetamido-2-fluorobenzene-1-sulfonyl chloride (1.47 g, 5.84 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (0.870 g, 5.84 mmol), triethylamine (8.2 mL, 58.4 mmol), and N,N-dimethylformamide (30 mL) was stirred for one hour at room temperature. The solution was then made to pH 5 using 6 N hydrochloric acid. The solution was then extracted using ethyl acetate and water. The organic layer was washed five times with water, and then washed with brine. The organic layer was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give N-(3-fluoro-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetamide (1.57 g, 74% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 2.04 (s, 3H), 4.85 (s, 2H), 7.17 (dd, J=2.1 Hz, J=8.2 Hz, 1H), 7.24 (d, J=8.2 Hz, 1H), 7.30 (dd, J=1.8 Hz, J=8.7 Hz, 1H), 7.45 (d, J=1.7 Hz, 1H), 7.65-7.70 (m, 2H), 9.19 (s, 1H), 10.41 (s, 1H), 10.44 (s, 1H)

Workup

  1. extractionThe solution was then extracted
  2. washThe organic layer was washed five times with water
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fb211ebd71b148b89e2df4a5c7d5392d
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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