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

HRID 511158Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18](=O)[CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14][CH2:13]2)=[CH:7][C:6]=1[C:39]([F:42])([F:41])[F:40])(=[O:4])=[O:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:52])=CC=1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18](=[S:52])[CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14][CH2:13]2)=[CH:7][C:6]=1[C:39]([F:42])([F:41])[F:40])(=[O:4])=[O:3]

Participants

Reactant 2

HCID 87949Lawesson's reagent

HCID 469467681-[4-(4-Methanesulfonyl-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-4-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-butan-1-one

Product 1

HCID 585763311-[4-(4-Methanesulfonyl-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-4-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-butane-1-thione

Procedure

1-[4-(4-Methanesulfonyl-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-4-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-butan-1-one (7 mg; 0.011 mmol, prepared in accordance with Example 30) is reacted with Lawesson's reagent (2 mg; 0.006 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=637; observed mass=637; HPLC retention time=4.48 min.

Sources & evidence

ORD record: ord-138852bfee6141dda798928f046e9d95
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

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