Ethyl isocyanate → 4-Amino-2-(3-ethylureido)-N-(1-hydroxy-1,3-dihydrobenzo[c][1, 2]oxaborol-6-yl)benzenesulfonamide

HRID 1256178Notes

Reaction equation

HRID 1256178 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][C:16]2[CH2:20][O:19][B:18]([OH:21])[C:17]=2[CH:22]=1)(=[O:11])=[O:10].[N:23]([CH2:26][CH3:27])=[C:24]=[O:25]>CN(C=O)C.C(OCC)(=O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([S:9]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[CH2:20][O:19][B:18]([OH:21])[C:17]=3[CH:22]=2)(=[O:10])=[O:11])=[C:2]([NH:1][C:24]([NH:23][CH2:26][CH3:27])=[O:25])[CH:7]=1

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 671737422,4-diamino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

Product 1

HCID 673124054-Amino-2-(3-ethylureido)-N-(1-hydroxy-1,3-dihydrobenzo[c][1, 2]oxaborol-6-yl)benzenesulfonamideYield 24.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-diamino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (1.0 g, 3.13 mmol) in DMF (15 ml) was added isocyanatoethane (0.5 g, 7.0 mmol) dropwise at room temperature. The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate and washed with H2O, brine. The organic fraction was then dried (MgSO4) and concentrated in vacuo. The residue was purified by Prep-HPLC to give the title compound as a white powder (0.3 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.87 (s, 1H), 9.17 (s, 1H), 7.99 (s, 1H), 7.43 (d, J=1.6 Hz, 1H), 7.34 (d, J=2.0 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 7.24 (d, J=8.0 Hz, 1H), 7.12 (dd, J=2.0, 8.4 Hz, 1H), 7.02 (t, J=5.2 Hz, 1H), 6.08 (dd, J=2.0, 8.4 Hz, 1H), 5.88 (s, 2H), 4.87 (s, 2H), 3.04˜3.11 (m, 2H), 1.07 (t, J=7.2 Hz, 3H); MS (ESI) m/z=389 (M−1, negative); HPLC purity: 93.6% (MaxPlot 200-400 nm), 90.3% (220 nm).

Workup

  1. washwashed with H2O, brine
  2. dry with materialThe organic fraction was then dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-2d30f9293bc54d8c9f56c0963618fa40
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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