HCID 86665952, compound → HCID 49820500, compound

HRID 1024676Notes

Reaction equation

HRID 1024676 reaction equation
C([N:4](O)[C:5]([C:7]1[CH:44]=[CH:43][C:10]([O:11][C:12]2[C:17]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25](F)=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[CH:16][CH:15]=[C:14]([O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36](=[NH:42])[N:37](O)C(=O)C)=[CH:32][CH:31]=3)[N:13]=2)=[CH:9][CH:8]=1)=[NH:6])(=O)C>CO.[Pd]>[C:5]([C:7]1[CH:44]=[CH:43][C:10]([O:11][C:12]2[C:17]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]4[C:24](=[CH:5][CH:7]=[CH:8][CH:9]=4)[CH:23]=3)(=[O:21])=[O:20])=[CH:16][CH:15]=[C:14]([O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36](=[NH:42])[NH2:37])=[CH:32][CH:31]=3)[N:13]=2)=[CH:9][CH:8]=1)(=[NH:6])[NH2:4]

Participants

4

Reactant 1

HCID 86665952HCID 86665952, compound

Product 1

HCID 49820500HCID 49820500, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

10% Pd/C (0.1 g) was added under an atmosphere of nitrogen gas to 2,6-bis-(4-(N-acetylhydroxycarbamimidoyl)-phenoxy)-3-(4-fluorobenzene-sulphonamido)-pyridine 0.3 g (0.44 mmol) dissolved in 50 ml methanol. 30 mg of 10% Pd/C was added under nitrogen atmosphere and the reaction mixture was stirred under hydrogen pressure (balloon) at room temperature for 3 h. The reaction mixture was passed through celite, washed with methanol and concentrated under reduced pressure. The concentrate was purified using reverse-phase preparative HPLC column to afford 0.06 g. of the required product. Percentage purity (HPLC): 85.01%, (LCMS): 82.73%. 1H NMR (DMSO-d6): 6.75 (2H, d), 6.9 (1H, d), 7.3 (2H, d), 7.5 (2H, d), 7.65 (2H, m), 7.8 (3H, d), 8.0 (4H, m), 8.35 (1H, s), 9.03 (4H, d), 9.2 (4H, s), 10.2 (1H, s).

Workup

  1. washwashed with methanol
  2. concentrationconcentrated under reduced pressure
  3. customThe concentrate was purified
  4. customto afford 0.06 g

Sources & evidence

ORD record
ord-7163cec126304ea38fea76cbaca54615
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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