Hydrazine hydrate (1:1) → HCID 86629534, compound

HRID 1711190Notes

Reaction equation

HRID 1711190 reaction equation
[Cl:1][C:2]1[CH:40]=[C:39]([CH3:41])[C:5]([C:6]([NH:8][CH2:9][CH2:10][CH:11]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C@H:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:21][N:22]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:15][CH2:14]2)[CH3:12])=[O:7])=[C:4]([CH3:42])[N:3]=1.O.NN>CCO>[NH2:22][CH2:21][C@H:20]([NH:19][CH:16]1[CH2:17][CH2:18][N:13]([CH:11]([CH3:12])[CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]2[C:39]([CH3:41])=[CH:40][C:2]([Cl:1])=[N:3][C:4]=2[CH3:42])[CH2:14][CH2:15]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86629535HCID 86629535, compound

Product 1

HCID 86629534HCID 86629534, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following general procedure D: a solution of 6-chloro-N-(3-{4-[(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1-phenyl-ethylamino]-piperidin-1-yl}-butyl)-2,4-dimethyl-nicotinamide (194 mg, 0.33 mmol), hydrazine hydrate (0.05 ml ml, 0.1 mmol) in EtOH (2 ml) was stirred at rt overnight. Purification of the crude product by chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 100:10:2) afforded N-{3-[4-((R)-2-Amino-1-phenyl-ethylamino)-piperidin-1-yl]-butyl}-6-chloro-2,4-dimethyl-nicotinamide (102 mg, 67%).

Workup

  1. customPurification of the crude product by chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 100:10:2)

Sources & evidence

ORD record
ord-6a1df33777a14d63b45942da84b86036
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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