Hydrazine, acetate (1:1) → HCID 68863971, compound

HRID 494124Notes

Reaction equation

HRID 494124 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]2[C:8]([C:18](=O)[C:19]([O:21][CH3:22])=[O:20])=[C:9]([C:13](OCC)=[O:14])[C:10]([O:11][CH3:12])=[C:4]2[C:3]1=[O:24].C(OC(NCC(N(CC(OC)OC)C)=O)=O)C1C=CC=CC=1.C(O)(=O)C.[NH2:51][NH2:52]>C(O)(=O)C>[CH3:12][O:11][C:10]1[C:9]2[C:13](=[O:14])[NH:52][N:51]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:8]=2[N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[C:3](=[O:24])[C:4]=12

Participants

5

Reactant 3

HCID 165591Hydrazine, acetate (1:1)HCID 58009747HCID 58009747, compoundHCID 68865401HCID 68865401, compound

Product 1

HCID 68863971HCID 68863971, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
160 °C

Procedure

A solution of ethyl 2-methyl-8-(methoxy)-6-[methoxy(oxo)acetyl]-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate (1.28 g, 3.78 mmol; prepared in a manner similar to that described in Example 62, step 5 to 8, starting with 1-methylpiperazin-2-one (Example 7, step 1 to 3) and hydrazine acetate (1.05 g, 11.36 mmol) in glacial acetic acid (8 mL) was heated at 160° C. in an microwave oven for 20 minutes. The mixture was concentrated under vacuum. The residue was partitioned between chloroform and brine. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was triturated in a 4:1 mixture of ethanol and diethyl ether. The precipitate was filtered to afford the title compound. ES MS M+1=321

Workup

  1. customprepared in a manner similar to
  2. concentrationThe mixture was concentrated under vacuum
  3. customThe residue was partitioned between chloroform and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was triturated in a 4:1 mixture of ethanol and diethyl ether
  9. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-91fb736e81e641519cdf14ef56ffe676
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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