3-Chloropropanesulphonyl chloride → [6-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)-4-methylpyridin-3-yl][4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411616Notes

Reaction equation

HRID 2411616 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[C:18]([CH3:24])[N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([CH3:25])[CH:3]=1.COC1C=C[C:31]([CH2:32][NH2:33])=[CH:30]C=1.ClCCC[S:40](Cl)(=[O:42])=[O:41].NC1N=CC(C(N2CCN(C3C(C4CC4)=CC(C)=CN=3)CC2)=O)=C(C)C=1>>[O:41]=[S:40]1(=[O:42])[CH2:30][CH2:31][CH2:32][N:33]1[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[C:18]([CH3:24])[N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([CH3:25])[CH:3]=1

Participants

5

Reactant 4

HCID 154103-Chloropropanesulphonyl chlorideHCID 754524-MethoxybenzylamineHCID 71252348(6-Amino-4-methylpyridin-3-yl)[4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazin-1-yl]methanoneHCID 71252523HCID 71252523, compound

Product 1

HCID 71252726[6-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)-4-methylpyridin-3-yl][4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone

Procedure

Using (6-fluoro-4-methylpyridin-3-yl)[4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone (220 mg) described in Preparation Example 182, 4-methoxybenzylamine (1.5 mL) and 3-chloropropane-1-sulfonyl chloride (0.16 mL) and by the reaction and treatment in the same manner as in Example 229, the title compound (175 mg) was obtained via (6-amino-4-methylpyridin-3-yl)[4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazin-1-yl]methanone.

Sources & evidence

ORD record
ord-9e9af3fcc431487a9ad51d55f0a89c90
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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