Hydrazine → HCID 11554690, compound

HRID 1443628Notes

Reaction equation

HRID 1443628 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH:17]([N:21]([CH2:31][CH2:32][CH2:33][N:34]1C(=O)C2C(=CC=CC=2)C1=O)[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[CH:18]([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C(O)C>[NH2:34][CH2:33][CH2:32][CH2:31][N:21]([C@@H:17]([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][CH:15]=[CH:16][C:11]=2[N:10]=1)[CH:18]([CH3:19])[CH3:20])[C:22](=[O:30])[C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 68560231HCID 68560231, compound

Product 1

HCID 11554690HCID 11554690, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[1-(1-benzyl-1H-benzimidazol-2-yl)-2-methyl-propyl]-N-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-4-chloro-benzamide (180 mg, 0.302 mmol) in ethanol at room temperature, was added hydrazine (0.19 ml, 6 mmol). The reaction was stirred at room temperature for 1 hour. The crude product was purified via reverse phase chromatography to give N-(3-aminopropyl)-N-[(1R)-1-(1-benzyl-1H-benzimidazol-2-yl)-2-methylpropyl]-4-chlorobenzamide 5 (129 mg, yield 91%).

Workup

  1. customThe crude product was purified via reverse phase chromatography

Sources & evidence

ORD record
ord-83422a018d954855b4966a0d5543d143
Source dataset
uspto-grants-2010_02
Patent number
US07662581B1

Reaction notes

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