2,4-Dichlorobenzoyl chloride → tert-Butyl 4-{[(2,4-dichlorobenzoyl)amino]methyl}-4-[3-(methoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate

HRID 1169845Notes

Reaction equation

HRID 1169845 reaction equation
[C:1]([C:3]1([C:16]2[C:21]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>[Ni]>[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29]([NH:2][CH2:1][C:3]1([C:16]2[C:21]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:30]

Participants

4

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 68896415Tert-butyl 4-cyano-4-[3-(methoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate

Product 1

HCID 66791411tert-Butyl 4-{[(2,4-dichlorobenzoyl)amino]methyl}-4-[3-(methoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

tert-Butyl 4-cyano-4-[3-(methoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate was reduced using Raney nickel and acylated using 2,4-dichlorobenzoyl chloride using the method exemplified in example 8-1 to afford the desired product: tert-butyl 4-{[(2,4-dichlorobenzoyl)amino]-methyl}-4-[3-(inethoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate: 1H NMR δ (ppm)(CDCl3): 8.18 (1 H, dd, J=1.3, 4.5 Hz), 7.50-7.46 (2 H, m), 7.33 (1 H, d, J=1.9 Hz), 7.25 (1 H, dd, J=8.3, 2.0), 7.15 (1 H, dd, J=4.6, 8.3 Hz), 6.70 (1 H, m), 5.25 (2 H, s), 4.01 (2 H, br s), 3.68-3.62 (2 H, m), 3.49 (3 H, s), 3.44-3.38 (2 H, m), 2.75-2.69 (2 H, m), 1.66-1.60 (1 H, m) 1.46 (9 H, s).

Sources & evidence

ORD record
ord-1a86862593224aebb545e97281f01a89
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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