Hydrazine → HCID 11627957, compound

HRID 1443636Notes

Reaction equation

HRID 1443636 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([Br:17])=[CH:16][C:11]=2[N:10]=[C:9]1[CH:18]([N:22]([CH2:32][CH2:33][CH2:34][N:35]1C(=O)C2C(=CC=CC=2)C1=O)[C:23](=[O:31])[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C(O)C>[NH2:35][CH2:34][CH2:33][CH2:32][N:22]([C@@H:18]([C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:12]2[CH:13]=[CH:14][C:15]([Br:17])=[CH:16][C:11]=2[N:10]=1)[CH:19]([CH3:20])[CH3:21])[C:23](=[O:31])[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 68561988HCID 68561988, compound

Product 1

HCID 11627957HCID 11627957, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[1-(1-benzyl-5-bromo-1H-benzimidazol-2-yl)-2-methyl-propyl]-N-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-4-methyl-benzamide (0.302 mmol) in ethanol at room temperature, was added hydrazine (0.19 ml, 6 mmol, 20 eq). The reaction was stirred at room temperature for 1 hour. The crude product was purified via reverse phase chromatography to give N-(3-amino-propyl)-N-[(1R)-1-(1-benzyl-5-bromo-1H-benzimidazol-2-yl)-2-methyl-propyl]-4-methyl-benzamide 6 (147 mg, yield 91%).

Workup

  1. customThe crude product was purified via reverse phase chromatography

Sources & evidence

ORD record
ord-e4ad559ff30c45da8839dcdfd96ab8fa
Source dataset
uspto-grants-2010_02
Patent number
US07662581B1

Reaction notes

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