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

HRID 511159Notes

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

Participants

Reactant 2

HCID 87949Lawesson's reagent

HCID 585767501-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(4-trifluoromethyl-benzyloxy)-piperidin-1-yl]-propan-1-one

Product 1

HCID 585771211-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(4-trifluoromethyl-benzyloxy)-piperidin-1-yl]-propane-1-thione

Procedure

1-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(4-fluoromethyl-benzyloxy)-piperidin-1-yl]-propan-1-one (26 mg; 0.043 mmol, prepared in accordance with Example 57) is reacted with Lawesson's reagent (9 mg; 0.022 mmol) according to the general conditions described in Example 109. The desired product is obtained following purification by preparative HPLC (7 mg; 0.011 mmol). The structure was confirmed using Protocol I-B. Calculated mass=619; observed mass=619; HPLC retention time=4.79 min.

Sources & evidence

ORD record: ord-5c998e430e8e4193b2b563225bfdcc6e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

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