Lawesson's reagent → 4-(1-{2-Methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-thiopropionyl}-piperidin-4-ylamino)-2-trifluoromethyl-benzonitrile

HRID 511162Notes

Reaction equation

[CH3:1][CH:2]([CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)[CH2:7][CH2:6]1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:50])=CC=1>>[CH3:1][CH:2]([CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)[CH2:7][CH2:6]1)=[S:50]

Participants

Reactant 2

HCID 87949Lawesson's reagent

HCID 585764544-(1-{2-Methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-propionyl}-piperidin-4-ylamino)-2-trifluoromethyl-benzonitrile

Product 1

HCID 585763134-(1-{2-Methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-thiopropionyl}-piperidin-4-ylamino)-2-trifluoromethyl-benzonitrile

Procedure

4-(1-{2-Methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-propionyl}-piperidin-4-ylamino)-2-trifluoromethyl-benzonitrile (15 mg; 0.026 mmol, prepared in accordance with Example 92) is reacted with Lawesson's reagent (5 mg; 0.013 mmol) according to the general conditions described in Example 109. The desired product is obtained following purification by preparative HPLC (9 mg; 0.015 mmol). The structure was confirmed using Protocol I-B. Calculated mass=584; observed mass=584; HPLC retention time=4.68 min

Sources & evidence

ORD record: ord-d82f2ea37f3947a5977972c4ce43ff81
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

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