Triethylamine → HCID 67311904, compound

HRID 1256137Notes

Reaction equation

HRID 1256137 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:37](Cl)(=[O:39])=[O:38])[CH2:36][CH2:35][CH2:34][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:37]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)(=[O:39])=[O:38])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 237554Cyclohexanesulfonyl chlorideHCID 671734224-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

Product 1

HCID 67311904HCID 67311904, compoundYield 13%

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 (0.6 g, 1.8 mmol) and triethylamine (0.7 mL, 5 mmol) in 100 mL of DCM was added cyclohexanesulfonyl chloride (0.3 g, 2.2 mmol). The reaction mixture was stirred at room temperature for 16 hours. After 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 powder (112 mg, yield 13%). MS calcd for (C20H26BN3O6S2): 479.1. MS found (ESI negative): (M−H)−=478.0. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.03 (s, 1H), 9.17 (bs, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.44 (d, J=2 Hz, 1H), 7.33 (t, J=6.4 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 7.10 (dd, J=8, 2 Hz, 1H), 6.81 (d, J=2 Hz, 1H), 6.40 (dd, J=8.8, 2.4 Hz, 1H), 4.86 (s, 2H), 4.44 (d, J=6.4 Hz, 2H), 2.93 (m, 1H), 2.02 (m, 2H), 1.80 (m, 2H), 1.64 (m, 1H), 1.33 (m, 5H).

Workup

  1. customAfter 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-7fe606ecc7a043909a7847a9d794abe5
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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