Methylhydrazine → N-[4-(2-{4-[(aminooxy)methyl]phenyl}ethyl)-1,3-thiazol-2-yl]acetamide

HRID 1246465Notes

Reaction equation

HRID 1246465 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([NH:27][C:28](=[O:30])[CH3:29])[S:25][CH:26]=2)=[CH:16][CH:15]=1.CNN>ClCCl>[NH2:3][O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([NH:27][C:28](=[O:30])[CH3:29])[S:25][CH:26]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 21915019N-{4-[2-(4-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl) oxy]methyl}phenyl)ethyl]-1,3-thiazol-2-yl}acetamide

Product 1

HCID 21914692N-[4-(2-{4-[(aminooxy)methyl]phenyl}ethyl)-1,3-thiazol-2-yl]acetamideYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-{4-[2-(4-{[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}phenyl)ethyl]-1,3-thiazol-2-yl}acetamide (200 mg), methylhydrazine (0.038 ml) and dichloromethane (4 ml) were combined under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1.5 hours, and filtered in vacuo. The filtrate was washed with saturated sodium hydrogen carbonate solution, water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residual solid was washed with acetonitrile to give N-[4-(2-{4-[(aminooxy)methyl]phenyl}ethyl)-1,3-thiazol-2-yl]acetamide (81.8 mg) as a colorless solid.

Workup

  1. filtrationfiltered in vacuo
  2. washThe filtrate was washed with saturated sodium hydrogen carbonate solution, water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washThe residual solid was washed with acetonitrile

Sources & evidence

ORD record
ord-d3e1ba074ca84f31bf49237023087a04
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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