Hydrazine → HCID 59656442, compound

HRID 2054888Notes

Reaction equation

HRID 2054888 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-9432556cbab048699d1864dfec599d57
Source dataset
uspto-grants-2008_02
Patent number
US07329755B2

Reaction notes

Loading…