Lawesson's reagent → HCID 58576480, compound

HRID 511152Notes

Reaction equation

HRID 511152 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]3[CH2:25][CH2:24][CH:23]([NH:26][C:27]4[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=4)[CH2:22][CH2:21]3)=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1>>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]3[CH2:25][CH2:24][CH:23]([NH:26][C:27]4[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=4)[CH2:22][CH2:21]3)=[S:46])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 87949Lawesson's reagent2×HCID 46946366HCID 46946366, compound

Product 1

HCID 58576480HCID 58576480, compound

Conditions

Temperature
102.5 °C

Procedure

4-(1-{4-[4-(4-Trifluoromethyl-phenyl)-piperazin-1-yl]-butyryl}-piperidin-4-ylamino)-benzonitrile (7 mg; 0.014 mmol, prepared in accordance with Example 83) is reacted with Lawesson's reagent (3 mg; 0.007 mmol) and the resulting mixture is heated between at 95 to 110° C. for 2 hours. In cases where incomplete conversion of the starting amide is observed, additional portion of Lawesson's reagent is added and the mixture heated further until no evolution of the conversion is observed. The reaction mixture is concentrated under reduced pressure and the crude residue is purified by preparative HPLC (1 mg; 0.002 mmol). The structure was confirmed using Protocol I-B. Calculated mass=516; observed mass=516; HPLC retention time=4.53 min.

Workup

  1. temperaturethe mixture heated further until no evolution of the conversion
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customthe crude residue is purified by preparative HPLC (1 mg; 0.002 mmol)

Sources & evidence

ORD record
ord-9489e99577214ffa8ed6424fc1e16fd8
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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