Hydrazine → (2R,5S)-2-Amino-ethanesulfonic acid 5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamide

HRID 480199Notes

Reaction equation

HRID 480199 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH2:27][C:28]([N:30]2[CH2:35][C@H:34]([CH3:36])[N:33]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)[CH2:32][C@H:31]2[CH3:45])=[O:29])=[C:6]([CH:25]=1)[CH2:7][NH:8][S:9]([CH2:12][CH2:13][N:14]1C(=O)C2C(=CC=CC=2)C1=O)(=[O:11])=[O:10].NN>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH2:27][C:28]([N:30]2[CH2:35][C@H:34]([CH3:36])[N:33]([CH2:37][C:38]3[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=3)[CH2:32][C@H:31]2[CH3:45])=[O:29])=[C:6]([CH:25]=1)[CH2:7][NH:8][S:9]([CH2:12][CH2:13][NH2:14])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 69911897HCID 69911897, compound

Product 1

HCID 12112115(2R,5S)-2-Amino-ethanesulfonic acid 5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamideYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R,5S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid 5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamide (0.073 g, 0.111 mmol) in EtOH (1 mL) was added hydrazine (35% aq. 0.25 mL, 2.73 mmol) and the solution was stirred overnight at ambient temperature. The reaction was filtered through a glass frit and washed with EtOH. The filtrate was concentrated in vacuo to give the title compound (0.056 g, 96%)

Workup

  1. filtrationThe reaction was filtered through a glass frit
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b002670f7ddb4562a4216374650a1d6f
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

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