2,6-Dichloropyridine → HCID 57430017, compound

HRID 1169843Notes

Reaction equation

HRID 1169843 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[C:9]([CH:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1)#[N:10].[Cl:24][C:25]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28].[CH2:35]([S:38](Cl)(=[O:40])=[O:39])[CH2:36][CH3:37]>[Ni]>[Cl:24][C:25]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:26]=1[C:27]([NH:10][CH2:9][C:11]1([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=2)[CH2:12][CH2:13][N:14]([S:38]([CH2:35][CH2:36][CH3:37])(=[O:40])=[O:39])[CH2:15][CH2:16]1)=[O:28]

Participants

6

Reactant 4

HCID 169892,6-DichloropyridineHCID 662791-Propanesulfonyl chlorideHCID 666452,4-Dichlorobenzoyl chlorideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylate

Product 1

HCID 57430017HCID 57430017, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

2,6-Dichloropyridine was reacted with tert-butyl 4-cyanopiperidine-1-carboxylate, reduced using Raney nickel, acylated with 2,4-dichlorobenzoyl chloride, deprotected and then sulphonylated with 1-propane sulphonyl chloride using the method described in example 10-2 to afford the desired product: 2,4-dichloro-N-{[4-(6-chloropyridin-2-yl)-1-propylsulfonyl)piperidin-4-yl]methyl}benzamide: 1H NMR δ (ppm)(CDCl3): 7.69 (1 H, t, J=7.8 Hz), 7.63 (1 H, d, J=8.3 Hz), 7.40 (1 H, d, J=1.9 Hz), 7.32-7.30 (2 H, m), 7.24 (1 H, d, J=7.8 Hz), 6.94 (1 H, m), 3.89 (2 H, d, J=6.2 Hz), 3.48-3.40 (4 H, m), 2.91-2.89 (2 H, m), 2.29-2.23 (2 H, m), 1.99-1.95 (2 H, m), 1.88-1.81 (2 H, m), 1.06 (3 H, t, J=7.4 Hz), m/z (ES) 504, 506 (M+H).

Sources & evidence

ORD record
ord-dcc76fa388354c0787a53e7bbec90608
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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