Hydrazine → tert-Butyl 1-[6-chloro-4-(hydrazinocarbonyl)pyridin-2-yl]piperidin-4-ylcarbamate

HRID 2233844Notes

Reaction equation

HRID 2233844 reaction equation
[NH2:1][NH2:2].[C:3]([O:7][C:8]([NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[C:19]([CH:24]=[C:25]([Cl:27])[N:26]=2)[C:20](OC)=[O:21])[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)(C)C>[Cl:27][C:25]1[N:26]=[C:17]([N:14]2[CH2:13][CH2:12][CH:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:4])([CH3:5])[CH3:6])[CH2:16][CH2:15]2)[CH:18]=[C:19]([C:20]([NH:1][NH2:2])=[O:21])[CH:24]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86608242Methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6-chloroisonicotinate2×

Product 1

HCID 86608244tert-Butyl 1-[6-chloro-4-(hydrazinocarbonyl)pyridin-2-yl]piperidin-4-ylcarbamateYield 87.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Hydrazine (0.55 ml 17.0 mmol) was added to a solution of methyl 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6-chloroisonicotinate (Intermediate 23, 0.15 g, 0.40 mmol) in isopropanol (3 ml). The mixture was stirred at room temperature overnight then the isopropanol was removed in vacuo to give the title product (130 mg).

Workup

  1. customthe isopropanol was removed in vacuo

Sources & evidence

ORD record
ord-d153e6a1920144729eb5b48f5d035018
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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