Hydrazine hydrate (1:1) → HCID 86650763, compound

HRID 875233Notes

Reaction equation

HRID 875233 reaction equation
[CH3:1][C:2]1[C:3]([C:9](=[N:16][O:17][CH2:18][C:19]2[N:24]=[C:23]([N:25]3C(=O)C4C(=CC=CC=4)C3=O)[CH:22]=[CH:21][CH:20]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][C:5]([CH3:8])=[CH:6][N:7]=1.O.NN>O1CCCC1>[CH3:1][C:2]1[C:3]([C:9](=[N:16][O:17][CH2:18][C:19]2[N:24]=[C:23]([NH2:25])[CH:22]=[CH:21][CH:20]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:4][C:5]([CH3:8])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86650762HCID 86650762, compound

Product 1

HCID 86650763HCID 86650763, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{6-[({[(3,6-dimethylpyrazin-2-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione (4.08 g, 8.80 mmol) in tetrahydrofuran (60 mL) was added dropwise hydrazine hydrate (2.14 mL, 44.0 mmol). After stirring at room temperature for 6 h, the reaction mixture was filtered, the insolubles washed with ethyl acetate, and the combined filtrates concentrated in vacuo, diluted in ethyl acetate (100 mL), washed with water (70 mL), dried over MgSO4 and concentrated to dryness in vacuo. Purification on silica gel afforded 6-[({[(3,6-dimethylpyrazin-2-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine [1.97 g, yield 64%; HPLC/MS: m/z=334 (M+H); log P(HCOOH)=1.31].

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe insolubles washed with ethyl acetate
  3. concentrationthe combined filtrates concentrated in vacuo
  4. additiondiluted in ethyl acetate (100 mL)
  5. washwashed with water (70 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness in vacuo
  8. customPurification on silica gel

Sources & evidence

ORD record
ord-51a8b8f26f9b4d85863310879be7f1b8
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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