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

HRID 1256094Notes

Reaction equation

HRID 1256094 reaction equation
[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([NH:26]C(=O)C(F)(F)F)[CH:9]=[CH:10][C:11]=1[S:12](=[O:25])(=[O:24])[NH:13][C:14]1[CH:15]=[CH:16][C:17]2[CH2:21][O:20][B:19]([OH:22])[C:18]=2[CH:23]=1)[CH3:2]>N.CO.[Pd]>[NH2:26][C:8]1[CH:9]=[CH:10][C:11]([S:12]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)(=[O:24])=[O:25])=[C:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH:7]=1

Participants

5

Reactant 1

HCID 86655212(E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 671737834-amino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(2-ethoxyethyl)benzenesulfonamideYield 47.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

(E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide (47 mg) was hydrogenated with Pd/C (10%, 20 mg) in 7N NH3 in methanol (6 ml) at 50 psi for 4 hrs. The catalyst was filtered and filtrate was concentrated to dryness. The crude product was purified by prep-HPLC to give 4-amino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(2-ethoxyethyl)benzenesulfonamide (18 mg). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.97 (s, 1H), 9.15 (s, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.39 (d, J=1.9 Hz, 1H), 7.21 (d, J=8.4 Hz, 1H), 7.10 (dd, J=2.2, 8.2 Hz, 1H), 6.42 (d, J=2.2 Hz, 1H), 6.34 (dd, J=2.0, 8.4 Hz, 1H), 5.84 (brs, 2H), 4.84 (s, 2H), 3.50 (t, J=7.2 Hz, 2H), 3.40 (q, J=7.1 Hz, 2H), 3.03 (t, J=7.1 Hz, 2H), 1.08 (t, J=7.0 Hz, 3H). MS (ESI) m/z=375 (M−1).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationfiltrate was concentrated to dryness
  3. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-00e1d95928bb4377bd1e51510877568c
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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