Hydrazine hydrate (1:1) → HCID 59954338, compound

HRID 1976244Notes

Reaction equation

HRID 1976244 reaction equation
O.NN.[C:4]1([C:10]2[CH:50]=[CH:49][CH:48]=[CH:47][C:11]=2[C:12]([NH:14][C:15]2[CH:46]=[CH:45][C:18]([C:19]([N:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]4[CH2:31][C@@H:32]([N:34]5C(=O)C6=CC=CC=C6C5=O)[CH2:33][C@H:23]4[CH2:22]3)=[O:20])=[CH:17][CH:16]=2)=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[NH2:34][C@@H:32]1[CH2:31][N:24]2[C:25]3[C:30]([N:21]([C:19](=[O:20])[C:18]4[CH:17]=[CH:16][C:15]([NH:14][C:12](=[O:13])[C:11]5[CH:47]=[CH:48][CH:49]=[CH:50][C:10]=5[C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=5)=[CH:46][CH:45]=4)[CH2:22][C@@H:23]2[CH2:33]1)=[CH:29][CH:28]=[CH:27][CH:26]=3

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59954332HCID 59954332, compound

Product 1

HCID 59954338HCID 59954338, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (0.41 g) was added to a solution of (2S, 3aS)-5-[4-[(2-phenylbenzoyl)amino]benzoyl]-2-phthalimido-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxaline (1.0 g) prepared in Reference Example 65 in ethanol (10 ml) and the mixture was heated under reflux conditions for one and half hours. After cooling the reaction solution, the ethanol was removed through concentration. The resulting residue was dissolved in chloroform, the resulting solution was washed with a 5% aqueous solution of sodium hydroxide and water, died over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography and then eluted with chloroform/methanol (95/5) to give 0.68 g (yield 86.0%) of the title compound as amorphous powder.

Workup

  1. temperaturethe mixture was heated under reflux conditions for one and half hours
  2. temperatureAfter cooling the reaction solution
  3. customthe ethanol was removed through concentration
  4. dissolutionThe resulting residue was dissolved in chloroform
  5. washthe resulting solution was washed with a 5% aqueous solution of sodium hydroxide and water
  6. concentrationconcentrated
  7. washeluted with chloroform/methanol (95/5)

Sources & evidence

ORD record
ord-102f97076ddc4b398d8930957051185c
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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