2-Amino-4-chloropyridine → 1-(t-Butoxycarbonyl)-4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-piperidine

HRID 1068223Notes

Reaction equation

HRID 1068223 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14](Br)[CH:15]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][N:20]=1>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:20]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]3=[N:18][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5818662-Amino-4-chloropyridineHCID 21912701tert-Butyl 4-(1-bromo-2-oxoethyl)piperidine-1-carboxylate

Product 1

HCID 211930101-(t-Butoxycarbonyl)-4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-piperidineYield 62.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from 350 mg of 1-(t-butoxycarbonyl)-4-(1-bromo-2-oxoethyl)-piperidine (from Example 292, Step C) and 162 mg of 2-amino-4-chloropyridine (prepared using procedures analogous to those described by R. J. Sundberg et al, Org. Preparations & Procedures Int. 1997, 29, (1), 117-122) in 10 mL ethanol using a procedure analogous to that described in Example 235, Step A to provide 240 mg of the title compound as a solid.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-d2c4c230d82b40fbbc8b8b5deb128607
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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