Hydrazine hydrate (1:1) → HCID 22046500, compound

HRID 1821779Notes

Reaction equation

HRID 1821779 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[N:14]=[CH:15][C:16]([NH:19][C:20]([NH:22][C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])=[O:21])=[N:17][CH:18]=1.O.NN>CCO.CN(C=O)C>[NH2:3][CH2:12][C:13]1[N:14]=[CH:15][C:16]([NH:19][C:20]([NH:22][C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])=[O:21])=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22046519HCID 22046519, compound

Product 1

HCID 22046500HCID 22046500, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-[5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-pyrazin-2-yl]-3-(2-methoxy-5-methyl-phenyl)-urea (16 mg, 38 μmol) in 380 μL 95% EtOH and 100 μL DMF at room temperature in a capped reaction vial was added hydrazine monohydrate (3.8 μL, 76 μmol). After stirring overnight at room temperature, a white precipitate formed. The precipitate was filtered off, dried and triturated with EtOAc to remove phthalimide based impurities to provide the product as a white solid (7.9 mg, 72%). 1H-NMR (400 MHz, d6-DMSO) δ 9.54 (s, 1H), 8.80 (s, 1H), 8.46 (s, 1H), 8.02 (s, 1H), 6.93 (d, 1H), 6.79 (d, 1H), 4.51 (d, 2H), 4.39 (br s, 2H), 3.89 (s, 3H), 2.23 (s, 3H). LRLCMS (ESI, Positive) m/e 288.2 (M+1).

Workup

  1. customa white precipitate formed
  2. filtrationThe precipitate was filtered off
  3. customdried
  4. customtriturated with EtOAc
  5. customto remove phthalimide based impurities

Sources & evidence

ORD record
ord-50bb29a9342748efab53b52ba31fac14
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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