Acetic Acid → HCID 68865233, compound

HRID 494154Notes

Reaction equation

HRID 494154 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[N:14]=[C:13]([C:28](=O)[CH2:29][NH:30][NH:31][C:32]([NH2:34])=[O:33])[C:12]=2[N:11]2[CH2:36][CH2:37][N:38]([CH3:41])[C:39](=[O:40])[C:10]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>C(O)C>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[F:26])[CH2:19][N:15]1[C:16](=[O:18])[C:17]2[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]3[C:39](=[O:40])[N:38]([CH3:41])[CH2:37][CH2:36][N:11]3[C:12]=2[C:13]([C:28]2[CH2:29][NH:30][NH:31][C:32](=[O:33])[N:34]=2)=[N:14]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 68864498HCID 68864498, compound

Product 1

HCID 68865233HCID 68865233, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the above hydrazinecarboxamide (0.20 g, 0.34 mmol) and glacial acetic acid (0.1 mL) in absolute ethanol (5 mL) was heated in a sealed tube in an oil bath at 100° C. overnight. The reaction mixture was concentrated under vacuum. The residue was partitioned between chloroform and aqueous sodium bicarbonate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the corresponding cyclized trazinyl intermediate. ES MS M+1=564

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe residue was partitioned between chloroform and aqueous sodium bicarbonate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto provide the corresponding cyclized trazinyl intermediate

Sources & evidence

ORD record
ord-c114921ac42743a9bd6e0107def5d3d1
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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