4-[(6-Chloro-pyridine-3-carbonyl)-amino]-4-cyano-piperidine-1-carboxylic acid tert-butyl ester → 6-Chloro-N-(4-cyano-piperidin-4-yl)-nicotinamide dihydrochloride

HRID 913338Notes

Reaction equation

HRID 913338 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([NH:16][C:17]([C:19]2[CH:20]=[N:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[O:18])([C:14]#[N:15])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[ClH:25].[ClH:25].[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]([NH:16][C:11]2([C:14]#[N:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:18])=[CH:20][N:21]=1

Participants

4

Reactant 1

HCID 866250164-[(6-Chloro-pyridine-3-carbonyl)-amino]-4-cyano-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866250176-Chloro-N-(4-cyano-piperidin-4-yl)-nicotinamide dihydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-[(6-chloro-pyridine-3-carbonyl)-amino]-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (0.30 g, 0.82 mmol) in 4 M HCl in dioxane (4 mL) was stirred at rt for 1 h. The solvent was removed under reduced pressure and the crude product used in the consecutive step without further purification assuming quantitative deprotection and formation of the dihydrochloride salt. Note: The product is contaminated with some primary amide (partial hydrolysis of the nitrile). MS (ISP): 265.3 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product used in the consecutive step without further purification
  3. custompartial hydrolysis of the nitrile)

Sources & evidence

ORD record
ord-b8bb5e4dba2b4d47a60a0b9ca4d80206
Source dataset
uspto-grants-2011_09
Patent number
US08026365B2

Reaction notes

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