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

HRID 1068228Notes

Reaction equation

HRID 1068228 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]([O:25][CH3:26])[CH:22]=[CH:21][N:20]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:20]3[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:19]3=[N:18][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 108987152-Amino-4-MethoxypyridineHCID 21912701tert-Butyl 4-(1-bromo-2-oxoethyl)piperidine-1-carboxylate

Product 1

HCID 211929571-(t-Butoxycarbonyl)4-(7-methoxy-imidazo[1,2-a]pyridin-3-yl)piperidine

Procedure

The title compound was prepared from 1-(t-butoxycarbonyl)-4-(1-bromo-2-oxoethyl)-piperidine (from Example 292, Step C) and 2-amino-4-methoxypyridine (prepared using procedures analogous to those described by R. J. Sundberg et al, Org. Preparations & Procedures Int. 1997, 29, (1), 117-122) using a procedure similar to that described in Example 235 Step A. 1H NMR (500 MHz, CDCl3): δ 1.50 (s, 9H), 1.63˜1.75 (m, 2H), 2.05 (br d, J=13 Hz, 2H), 2.85˜3.00 (br, 3H), 3.88 (s, 3H), 4.15˜4.35 (br, 2H), 6.58 (d, J=7.4 Hz, 1H), 6.93 (br s, 1H), 7.25 (br s, 1H), 7.79 (d, J=7.5 Hz, 1H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-360b226563794e6b95c2777da376ec2d
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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