Hydrazine hydrate (1:1) → (2r)-2-Amino-ethanesulfonic acid (5-chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-amide

HRID 480191Notes

Reaction equation

HRID 480191 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[CH2:31][CH:30]2[CH3:43])=[O:28])=[C:6]([NH:8][S:9]([CH2:12][CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)(=[O:11])=[O:10])[CH:7]=1.O.NN>CCO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH2:35][C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)[CH2:31][C@H:30]2[CH3:43])=[O:28])=[C:6]([NH:8][S:9]([CH2:12][CH2:13][NH2:14])(=[O:11])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 699590132-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (5-chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-amide

Product 1

HCID 12112110(2r)-2-Amino-ethanesulfonic acid (5-chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-amideYield 58.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (5-chloro-2-{2-[4-(4-fluoro-benzyl)-2-methyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-amide (0.030 g, 0.048 mmol) in EtOH (1 mL) at ambient temperature was added hydrazine hydrate (0.025 mL). The reaction was stirred overnight at ambient temperature then diluted with water and extracted with methylene chloride (2×). The combined organics were washed with saturated aqueous brine and dried over sodium sulfate, filtered and concentrated in vacuo. Purification via radial chromatography (2 mm plate) gave the title compound (0.014 g).

Workup

  1. extractionextracted with methylene chloride (2×)
  2. washThe combined organics were washed with saturated aqueous brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via radial chromatography (2 mm plate)

Sources & evidence

ORD record
ord-f715768bd85649cbba57cb407438bbca
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

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