Hydrochloric Acid → HCID 53234370, compound

HRID 1256101Notes

Reaction equation

HRID 1256101 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=3[CH2:24][CH2:25][O:26][CH3:27])(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1.Cl>CO.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]3[CH2:4][O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)(=[O:13])=[O:14])=[C:16]([CH2:24][CH2:25][O:26][CH3:27])[CH:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67175502HCID 67175502, compound

Product 1

HCID 53234370HCID 53234370, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(2-methoxyethyl)-4-nitrobenzenesulfonamide (1 g, crude, 2.5 mmol) and Pd/C (0.2 g, 10%) in MeOH (50 mL) was stirred under 50 PSI H2 at room temperature for 2 hrs. The mixture was filtered and the filtrate was concentrated. The residue was purified by prep-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 5%-35%, 23 min), concentrated, acidified with HCl and freeze-dried to give the title compound (0.3 g, yield 32%) as HCl salt. 1H NMR: 400 MHz DMSO-d6 δ10.01 (s, 1H), 7.56-7.54 (m, 1H), 7.40-7.39 (m, 1H), 7.21-7.18 (m, 1H), 7.11-7.09 (m, 1H), 6.48-6.40 (m, 2H), 4.83 (s, 2H), 3.49-3.45 (m, 2H), 3.21 (s, 3H), 3.06-3.03 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by prep-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 5%-35%, 23 min)
  4. concentrationconcentrated
  5. customfreeze-dried

Sources & evidence

ORD record
ord-5c45dff72ded4272a10bed9e11250fb0
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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