Dichloromethane → HCID 67310239, compound

HRID 1256135Notes

Reaction equation

HRID 1256135 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(Cl)Cl.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](=[O:9])(=[O:10])[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)=[C:4]([CH:3]=1)[CH2:22][NH:23][C:27](=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 671734224-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

Product 1

HCID 67310239HCID 67310239, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (500 mg, 1.5 mmol) in pyridine (15 ml) was stirred at room temperature for 30 mins. DCM (40 ml) and acetic anhydride (168 mg, 1.65 mmol) was then added to the mixture. And it was stirred at room temperature for overnight. The mixture was concentrated in vacuo and the residue was purified by prep. HPLC (column: Luna 300×50.0 mm, 10 u; liquid phase: [A-H2O+0.025% TFA; B-MeCN] B %: 10%-30%, 20 min) to give the title compound (226 mg, 40.2%) as a light yellow solid. 1H NMR: DMSO 400 MHz. δ9.99 (s, 1H), 9.19 (s, 1H), 8.24 (d, J=12.0 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.43 (s, 1H), 7.21 (d, J=8.0 Hz, 1H), 7.12 (dd, J=10.0 Hz, 1H), 6.45 (s, 1H), 6.35 (dd, J=10.8 Hz, 1H), 5.95 (brs, 2H), 4.85 (s, 2H), 4.54 (s, 2H), 1.92 (s, 3H). ESI-MS m/z 374 (M−H, positive); HPLC purity: 90.13% (MaxPlot 190-370 nm), 96.33% (220 nm).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-63b0fd973a364b6bb5ad469fc2af5c84
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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