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

HRID 2411598Notes

Reaction equation

HRID 2411598 reaction equation
C1(C2C=C(C)C(N3CCN(C(C4C=NC(F)=CC=4C)=O)CC3)=NC=2)CC1.COC1C=CC(CN)=CC=1.[Cl:37]CCCS(Cl)(=O)=O.NC1N=CC(C(N2CCN(C3C(C)=CC(C4CC4)=CN=3)CC2)=O)=C(C)C=1.[CH:71]1([C:74]2[CH:75]=[C:76]([CH3:102])[C:77]([N:80]3[CH2:85][CH2:84][N:83]([C:86]([C:88]4[CH:89]=[N:90][C:91]([N:95]5[CH2:99][CH2:98][CH2:97][S:96]5(=[O:101])=[O:100])=[CH:92][C:93]=4[CH3:94])=[O:87])[CH2:82][CH2:81]3)=[N:78][CH:79]=2)[CH2:73][CH2:72]1>>[ClH:37].[ClH:37].[CH:71]1([C:74]2[CH:75]=[C:76]([CH3:102])[C:77]([N:80]3[CH2:81][CH2:82][N:83]([C:86]([C:88]4[CH:89]=[N:90][C:91]([N:95]5[CH2:99][CH2:98][CH2:97][S:96]5(=[O:100])=[O:101])=[CH:92][C:93]=4[CH3:94])=[O:87])[CH2:84][CH2:85]3)=[N:78][CH:79]=2)[CH2:73][CH2:72]1

Participants

6

Reactant 5

HCID 154103-Chloropropanesulphonyl chlorideHCID 754524-MethoxybenzylamineHCID 58484562HCID 58484562, compoundHCID 71252201(6-Amino-4-methylpyridin-3-yl) [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanoneHCID 71252334[4-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][6-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-4-methylpyridin-3-yl]methanone

Product 1

HCID 86676784[4-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][6-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-4-methylpyridin-3-yl]methanone dihydrochloride

Procedure

Using [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl](6-fluoro-4-methylpyridin-3-yl)methanone (1.25 g) described in Preparation Example 140, 4-methoxybenzylamine (2 mL) and 3-chloropropane-1-sulfonyl chloride (0.55 ml) and by the reaction and treatment in the same manner as in Example 223, the title compound (950 mg) was obtained via (6-amino-4-methylpyridin-3-yl) [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone and [4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][6-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-4-methylpyridin-3-yl]methanone.

Sources & evidence

ORD record
ord-c3fff1a585fb48bda7c0cc068e39deb1
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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