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

HRID 511160Notes

Reaction equation

[CH3:1][C@@H:2]([CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([C:21]([F:24])([F:23])[F:22])[CH:13]=2)[CH2:7][CH2:6]1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:51])=CC=1>>[CH3:1][CH:2]([CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([C:21]([F:24])([F:23])[F:22])[CH:13]=2)[CH2:7][CH2:6]1)=[S:51]

Participants

Reactant 2

HCID 87949Lawesson's reagent

HCID 58576520(S)-2-methyl-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-propan-1-one

Product 1

HCID 585766202-Methyl-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-propane-1-thione

Procedure

2-Methyl-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-propane-1-thione (24 mg; 0.041 mmol, prepared in accordance with Example 68) is reacted with Lawesson's reagent (8 mg; 0.020 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=4.74 min.

Sources & evidence

ORD record: ord-853318d2c4b8481cb491dcceb79333bd
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

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