Methylhydrazine → HCID 21914962, compound

HRID 2117936Notes

Reaction equation

HRID 2117936 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:37][C:38](=[O:40])[CH3:39])[S:25][C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[CH:16][CH:15]=1.CNN>CN(C)C=O>[NH2:3][O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([NH:37][C:38](=[O:40])[CH3:39])[S:25][C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 21915241HCID 21915241, compound

Product 1

HCID 21914962HCID 21914962, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of N-{4-[2-(4-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}phenyl)ethyl]-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-2-yl}acetamide (116.8 mg) in N,N-dimethylformamide (1.1 ml) was added methylhydrazine (11.9 μl) under N2 atmosphere, and the mixture was stirred at 20° C. for 4 hrs. The reaction mixture was concentrated in vacuo. Ethyl acetate was added to the residue, and the precipitate was filtered off. The filtrate was concentrated in vacuo to give a crude yellow solid (105.1 mg). The crude material was purified by preparative thin-layer chromatography over silica gel with chloroform/methanol (30:1) as an eluent to give a pale yellow powder. The obtained powder was washed with acetonitrile, and the precipitate was collected by filtration to give N-{4-(2-{4-[(aminooxy)methyl]phenyl}ethyl)-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-2-yl}acetamide (8.4 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionEthyl acetate was added to the residue
  3. filtrationthe precipitate was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a crude yellow solid (105.1 mg)
  6. customThe crude material was purified by preparative thin-layer chromatography over silica gel with chloroform/methanol (30:1) as an eluent
  7. customto give a pale yellow powder
  8. washThe obtained powder was washed with acetonitrile
  9. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-cf1c00dce8324fc9b18b4afb75c39f37
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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