Hydrazine hydrate (1:1) → HCID 86751311, compound

HRID 1379204Notes

Reaction equation

HRID 1379204 reaction equation
[F:1][C:2]([F:46])([F:45])[C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH2:16][N:17]2C(=O)C3=CC=CC=C3C2=O)=[O:15])[CH2:10][C@H:9]1[CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)=[O:7].O.NN>C(O)C>[NH2:17][CH2:16][C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]2[CH:4]=[C:3]([C:2]([F:46])([F:1])[F:45])[CH:40]=[C:39]([C:41]([F:42])([F:43])[F:44])[CH:38]=2)[C@H:9]([CH2:28][C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:31][CH:30]=2)[CH2:10]1)=[O:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86751312HCID 86751312, compound

Product 1

HCID 86751311HCID 86751311, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)-4-(phthalimidomethylcarbonyl)piperazine (250 mg), hydrazine hydrate (50 mg) in ethanol (5 ml) was heated under reflux for 2 hours. The resulting precipitate was removed by filtration and the filtrate was evaporated under reduced pressure. The residue was washed with aqueous 1N sodium hydroxide solution and then purified by column chromatography on a silica gel eluting with a mixture of ethyl acetate and methanol (4:1) to afford (2R)-4-(2-aminoacetyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (110 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe resulting precipitate was removed by filtration
  4. customthe filtrate was evaporated under reduced pressure
  5. washThe residue was washed with aqueous 1N sodium hydroxide solution
  6. custompurified by column chromatography on a silica gel eluting with a mixture of ethyl acetate and methanol (4:1)

Sources & evidence

ORD record
ord-f0cbd21ab11e4ec496b15aab6079fe7a
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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