Hydrazine hydrate (1:1) → HCID 86650759, compound

HRID 875228Notes

Reaction equation

HRID 875228 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[N:13][O:14][CH2:15][C:16]2[N:21]=[C:20]([N:22]3C(=O)C4C(=CC=CC=4)C3=O)[CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)=[CH:5][N:4]=[CH:3]1.O.NN>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7](=[N:13][O:14][CH2:15][C:16]2[N:21]=[C:20]([NH2:22])[CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)=[CH:5][N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86650758HCID 86650758, compound

Product 1

HCID 86650759HCID 86650759, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{6-[({[(1-methyl-1H-imidazol-5-yl)(3-thienyl)methylene]amino}oxy)-methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione (6.80 g, 15.3 mmol) in tetrahydrofuran (30 mL) was added dropwise hydrazine hydrate (3.72 mL, 76.7 mmol). After stirring at room temperature for 30 h, the reaction mixture was filtered, the insolubles washed with ethyl acetate, and the filtrate concentrated in vacuo. Purification on silica gel afforded 6-[({[(1-methyl-1H-imidazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]pyridin-2-amine [3.02 g, yield 60%; HPLC/MS: m/z=314 (M+H); log P(HCOOH)=0.39].

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe insolubles washed with ethyl acetate
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification on silica gel

Sources & evidence

ORD record
ord-cd7b603ef5834632b0ac5e0ce8a0eec3
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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