Hydrazine hydrate (1:1) → HCID 18512083, compound

HRID 1370850Notes

Reaction equation

HRID 1370850 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][CH2:37][CH2:38][N:39]3C(=O)C4C(=CC=CC=4)C3=O)[CH:30]=2)=[CH:24][CH:23]=1)[C:9]1[C:10]([CH3:20])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CCO>[NH2:39][CH2:38][CH2:37][CH2:36][O:35][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=1)[O:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]2[C:10]([CH3:20])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18511916HCID 18511916, compound

Product 1

HCID 18512083HCID 18512083, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 70B (0.323 g, 0.479 mmoles) in EtOH (5 mL) was treated with hydrazine hydrate (0.15 mL, 4.79 mmoles). The reaction was heated overnight at 60 C. Reaction mixture concentrated under reduced pressure, and residue dissolved in ethyl acetate. The mixture was washed with H2O (2×), brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10% to 20% MeOH:CHCl3) to provide the title compound (0.160 g, 61%). MS (ESI+) m/z 546 (M+H)+.

Workup

  1. temperatureThe reaction was heated overnight at 60 C
  2. customReaction mixture
  3. concentrationconcentrated under reduced pressure, and residue
  4. dissolutiondissolved in ethyl acetate
  5. washThe mixture was washed with H2O (2×), brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, 10% to 20% MeOH:CHCl3)

Sources & evidence

ORD record
ord-7d4f37123ad04a95bc12cc36f6f2a291
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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