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

HRID 511156Notes

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][N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)[CH2:13][CH2:12]2)=[CH:6][C:5]=1[C:37]([F:40])([F:39])[F:38])([O-:3])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:50])=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:50])[CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)[CH2:13][CH2:12]2)=[CH:6][C:5]=1[C:37]([F:40])([F:39])[F:38])([O-:3])=[O:2]

Participants

Reactant 2

HCID 87949Lawesson's reagent

HCID 585766551-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(4-trifluoromethyl-phenyl)-piperidin-1-yl]-propan-1-one

Product 1

HCID 585766961-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(4-trifluoromethyl-phenyl)-piperidin-1-yl]-propane-1-thione

Procedure

1-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(4-trifluoromethyl-phenyl)-piperidin-1-yl]-propan-1-one (20 mg; 0.035 mmol, prepared in accordance with Example 14) is reacted with Lawesson's reagent (7 mg; 0.018 mmol according to the general conditions described in Example 109. The desired product is obtained following purification by preparative HPLC (6 mg; 0.010 mmol). The structure was confirmed using Protocol 1-B. Calculated mass=589; observed mass=589; HPLC retention time=4.74 min.

Sources & evidence

ORD record: ord-6ae7e691ca264d3db1e8428edb7cf6ff
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

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