Sodium periodate → HCID 86759982, compound

HRID 1795965Notes

Reaction equation

HRID 1795965 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][O:8][C:9]([C:11]1[CH:12]=[CH:13][N:14]2[C:19]=1[C:18](=[O:20])[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]([CH:28]=CN(C)C)=[N:15]2)=[O:10]>C1COCC1>[CH3:7][O:8][C:9]([C:11]1[CH:12]=[CH:13][N:14]2[C:19]=1[C:18](=[O:20])[N:17]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]([CH:28]=[O:2])=[N:15]2)=[O:10]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 86759981HCID 86759981, compound

Product 1

HCID 86759982HCID 86759982, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium periodate (0.52 g, 2.4 mmol) was added to pH 7 buffer solution (2.5 ml) of 3-benzyl-2-(2-dimethylamino-vinyl)-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-5-carboxylic acid methyl ester (0.17 g, 0.48 mmol) in THF (3.0 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was filtered through Celite® and the solids were washed with EtOAc (30 mL). The filtrate was washed with saturated NaCl (2×30 ml), dried (Na2SO4), filtered and concentrated in vacuo to afford the titled compound as a solid (0.15 g, 100%): 1H NMR (CDCl3) δ 9.41 (s, 1H), 7.16–7.40 (m, 7H), 5.68 (s, 2H), 3.88 (s, 3H); MS (ESI+) 312 (M++H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washthe solids were washed with EtOAc (30 mL)
  3. washThe filtrate was washed with saturated NaCl (2×30 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ccc282c2d7b14d2ebf569cd6e8f623a4
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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