Lawesson's reagent → 1-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-4-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-butane-1-thione

HRID 511161Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17](=O)[CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)[CH2:13][CH2:12]2)=[CH:6][C:5]=1[C:38]([F:41])([F:40])[F:39])([O-:3])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:51])=CC=1>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[S:51])[CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)[CH2:13][CH2:12]2)=[CH:6][C:5]=1[C:38]([F:41])([F:40])[F:39])([O-:3])=[O:2]

Participants

Reactant 2

HCID 87949Lawesson's reagent

HCID 58576421HCID 58576421, compound

Product 1

HCID 585769271-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-4-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-butane-1-thione

Procedure

1-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-4-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-butan-1-one (20 mg; 0.034 mmol, prepared in accordance with Example 165) is reacted with Lawesson's reagent (7 mg; 0.017 mmol) according to the general conditions described in Example 109. The desired product is obtained following purification by preparative HPLC (11 mg; 0.018 mmol). The structure was confirmed using Protocol I-B. Calculated mass=604; observed mass=604; HPLC retention time=4.64 min.

Sources & evidence

ORD record: ord-5f41a396cd174ce081533438c97ac00f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

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