Lawesson's reagent → 3-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-propane-1-thione

HRID 511155Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([CH3:38])[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([C:34]([F:37])([F:36])[F:35])[CH:26]=4)[CH2:20][CH2:19]3)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:48])=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([CH3:38])[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([C:34]([F:37])([F:36])[F:35])[CH:26]=4)[CH2:20][CH2:19]3)=[S:48])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 87949Lawesson's reagent

HCID 585769113-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-propan-1-one

Product 1

HCID 585768973-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-propane-1-thione

Procedure

3-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-propan-1-one (6 mg; 0.011 mmol, prepared in accordance with Example 61) is reacted with Lawesson's reagent (2 mg; 0.005 mmol) according to the general conditions described in Example 109. The desired product is obtained following purification by preparative HPLC (2 mg; 0.004 mmol). The structure was confirmed using Protocol I-B. Calculated mass=570; observed mass=570; HPLC retention time=4.69 min

Sources & evidence

ORD record: ord-60b9466b27d3423f835496f30b880b1b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

Loading…