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

HRID 1256136Notes

Reaction equation

HRID 1256136 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]3[CH2:19][O:18][B:17]([OH:20])[C:16]=3[CH:21]=2)(=[O:10])=[O:9])=[C:4]([CH2:22][NH2:23])[CH:3]=1.C(N(CC)CC)C.[CH:31]1([S:34](Cl)(=[O:36])=[O:35])[CH2:33][CH2:32]1>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]3[CH2:19][O:18][B:17]([OH:20])[C:16]=3[CH:21]=2)(=[O:9])=[O:10])=[C:4]([CH2:22][NH:23][S:34]([CH:31]2[CH2:33][CH2:32]2)(=[O:36])=[O:35])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 671734224-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

Product 1

HCID 532345374-Amino-2-(cyclopropanesulfonamidomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamideYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (708 mg, 2.1 mmol) and triethylamine (1 mL, 7 mmol) in 100 mL of DCM was added cyclopropanesulfonyl chloride (0.3 g, 2.2 mmol). The reaction mixture was stirred at room temperature for 16 hours. After the majority of the solvent was removed under vacuum, the reaction mixture was extracted with ethyl acetate and washed with water, 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated, the crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the desired product as a yellow solid (45 mg, yield 5%). MS calcd for (C17H20BN3O6S2): 437.1. MS found (ESI negative): (M−H)−=336.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.04 (s, 1H), 9.17 (bs, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.50 (t, J=6.4 Hz, 1H), 7.44 (d, J=1.6 Hz, 1H), 7.22 (d, J=8.8 Hz, 1H), 7.11 (dd, J=8, 1.6 Hz, 1H), 6.83 (d, J=2.4 Hz, 1H), 6.40 (dd, J=8.4, 2.4 Hz, 1H), 4.86 (s, 2H), 4.44 (d, J=6.4 Hz, 2H), 2.60 (m, 1H), 0.92 (m, 4H).

Workup

  1. customAfter the majority of the solvent was removed under vacuum
  2. extractionthe reaction mixture 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
  6. customthe crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-c4cecea8bb554a36b7e3e70ae9cd5652
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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