Lawesson's reagent → HCID 86647510, compound

HRID 2092085Notes

Reaction equation

HRID 2092085 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=O)[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10](=[S:40])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68430690HCID 68430690, compound

Product 1

HCID 86647510HCID 86647510, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

2-{5-Bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}-N-(pyridin-4-ylmethyl)acetamide (99 mg, 0.208 mmol) in toluene (1 mL) was mixed with Lawesson's reagent (168 mg, 0.416 mmol) and refluxed at 120° C. for 1 hour. After cooling, the reaction solution was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform/methanol=50/1) to give the desired product (28 mg, 27% yield).

Workup

  1. temperatureAfter cooling
  2. customthe reaction solution was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-b2fb259135c5464f83fb3ca73d9ff509
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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