Hydrazine → HCID 59656442, compound

HRID 2225124Notes

Reaction equation

HRID 2225124 reaction equation
[CH:1]1([NH:7][S:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][N:22]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.NN>CO>[CH:1]1([NH:7][S:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][NH2:22])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59656315HCID 59656315, compound

Product 1

HCID 59656442HCID 59656442, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-naphthalene-1-sulfonic acid cyclohexylamide (G-4) (1.6 g, 3.57 mmol) in methanol (30 mL) was added hydrazine (2 mL). The resultant solution was stirred at room temperature overnight. A precipitate was formed and filtered. The solid was further washed with small amount of methanol. The filtrate was collected and solvent was removed in vacuo. Flash chromatography of the residue with Flash column (MeOH/CH2Cl2: 5-10%) gave the title compound (42) as white solid (0.7 g). 1H NMR (300 MHz, DMSO) δ 8.68 (d, 1H), 8.24 (d, 1H), 8.13 (d, 1H), 7.60 (m, 3H), 5.00 (s, 1H), 4.39 (s, 2H), 3.10 (s, 1H), 2.03 (m, 2H), 1.59 (m, 4H), 1.08 (m, 4H); LC/MS m/z 319 (M+H)+.

Workup

  1. customA precipitate was formed
  2. filtrationfiltered
  3. washThe solid was further washed with small amount of methanol
  4. customThe filtrate was collected
  5. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-49c9744546b74ffbb9e8dc3bd93d48b7
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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