Triethylamine → 2-(5-Amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-N-(prop-2-ynyl)acetamide

HRID 1256129Notes

Reaction equation

HRID 1256129 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:25])(=[O:24])[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)=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.[CH2:26]([NH2:29])[C:27]#[CH:28].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:24])(=[O:25])[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)=[C:6]([CH2:8][C:9]([NH:29][CH2:26][C:27]#[CH:28])=[O:10])[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 239041PropargylamineHCID 2724699PyBOPHCID 53234452HCID 53234452, compound

Product 1

HCID 866552182-(5-Amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-N-(prop-2-ynyl)acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the mixture of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (363 mg, 1 mmol) and propargyl amine (0.2 ml, 3 mmol) in DMF (5 ml), added PyBOP (520 mg, 1 mmol) then triethyl amine (0.3 ml, 2 mmol). Stirring was kept for 3 hours. Diluted with EtOAc, washed with 1N HCl, water and brine. Dried over anhydrous sodium sulfate. Concentrated, the residue was dissolved in DMSO and purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column). The title compound was obtained as white powder. MS calcd for (C18H18BN3O5S): 399.11. MS found (ESI negative): (M−H)−=398.03. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.80 (s, 1H), 9.1 (br, 1H), 8.42 (t, J=4.8 Hz, 1H), 7.44 (s, 1H), 7.43 (d, J=8.4 Hz, 1H), 7.22 (d, J=8 Hz, 1H), 7.13 (dd, J=8.4 Hz, 1H), 6.44 (d, J=2 Hz, 1H), 6.36 (dd, J=8.8 Hz, 1H), 4.87 (s, 2H), 3.91 (m, 2H), 3.80 (s, 2H).

Workup

  1. washwashed with 1N HCl, water and brine
  2. dry with materialDried over anhydrous sodium sulfate
  3. concentrationConcentrated
  4. dissolutionthe residue was dissolved in DMSO
  5. custompurified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-53da7ecd194343bd8675299f4dfaf1a4
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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