Tert-butyl 4-{3-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-oxopropyl}-1-piperidinecarboxylate → 1-(6-Amino-5-chloro-2-methoxy-3-pyridinyl)-3-(4-piperidinyl)-1-propanone hydrochloride

HRID 489794Notes

Reaction equation

HRID 489794 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:26])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:27]>Cl>[ClH:27].[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:26])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:27]

Participants

3

Reactant 1

HCID 22262604Tert-butyl 4-{3-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-oxopropyl}-1-piperidinecarboxylate

Product 1

HCID 222625861-(6-Amino-5-chloro-2-methoxy-3-pyridinyl)-3-(4-piperidinyl)-1-propanone hydrochlorideYield 94.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of tert-butyl 4-{3-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-oxopropyl}-1-piperidinecarboxylate (step 5, 610 mg, 1.53 mmol) in 10% methanolic hydrochloric acid (6 ml) was stirred at room temperature for 18 h. The formed solid was collected by filtration, washed with methanol and dried to give 242.0 mg (47%) of the title compound as a white solid.

Workup

  1. filtrationThe formed solid was collected by filtration
  2. washwashed with methanol
  3. customdried

Sources & evidence

ORD record
ord-509e1b17f1d84e4b9e43e102ff5e38d4
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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