N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide → 4-amino-2-bromo-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

HRID 1256092Notes

Reaction equation

HRID 1256092 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:22]C(=O)C(F)(F)F)[CH:5]=[CH:6][C:7]=1[S:8](=[O:21])(=[O:20])[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:17][O:16][B:15]([OH:18])[C:14]=2[CH:19]=1>N.CO>[NH2:22][C:4]1[CH:5]=[CH:6][C:7]([S:8]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[CH2:17][O:16][B:15]([OH:18])[C:14]=3[CH:19]=2)(=[O:20])=[O:21])=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 1

HCID 86655204N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 532343694-amino-2-bromo-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamideYield 68.8%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide (200 mg) was dissolved in 7N NH3 in methanol and stirred at rt overnight. Evaporated to remove the solvent and purified by prep-HPLC to give 4-amino-2-bromo-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (110 mg). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.06 (s, 1H), 9.10 (brs, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.44 (d, J=2.0 Hz, 1H), 7.21 (d, J=8.4 Hz, 1H), 7.17 (dd, J=2.0, 8.4 Hz, 1H), 6.79 (d, J=2.0 Hz, 1H), 6.48 (dd, J=2.0, 8.4 Hz, 1H), 4.84 (s, 2H). MS (ESI) m/z=381 (M−1).

Workup

  1. customEvaporated
  2. customto remove the solvent
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-888ea0b7403a45bc8ef19440a15cc834
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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