Lawesson's reagent → HCID 58575988, compound

HRID 511157Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C:20]([N:22]3[CH2:27][CH2:26][CH:25]([NH:28][C:29]4[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[C:31]([C:38]([F:41])([F:40])[F:39])[CH:30]=4)[CH2:24][CH2:23]3)=O)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:51])=CC=1>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C:20]([N:22]3[CH2:27][CH2:26][CH:25]([NH:28][C:29]4[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[C:31]([C:38]([F:41])([F:40])[F:39])[CH:30]=4)[CH2:24][CH2:23]3)=[S:51])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 87949Lawesson's reagent

HCID 585760744-[4-(4-Tert-butyl-phenyl)-piperazin-1-yl]-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-butan-1-one

Product 1

HCID 58575988HCID 58575988, compound

Procedure

4-[4-(4-tert-Butyl-phenyl)-piperazin-1-yl]-1-[4-(4-nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-butan-1-one (28 mg; 0.049 mmol, prepared in accordance with Example 90) is reacted with Lawesson's reagent (10 mg; 0.024 mmol) according to the general conditions described in Example 109. The desired product is obtained following purification by preparative HPLC (13 mg; 0.023 mmol). The structure was confirmed using Protocol I-B. Calculated mass=592; observed mass=592; HPLC retention time=4.811 min.

Sources & evidence

ORD record: ord-046b618e81594502a67b2e376efca576
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096524B2

Reaction notes

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