Lawesson's reagent → HCID 58010113, compound

HRID 2204607Notes

Reaction equation

HRID 2204607 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH:3]1[C:18](=O)[CH2:19][NH:20][C:21]1[N:22]=[C:23]2[CH:29]=[CH:28][N:27]([S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:24]2=[N:25][CH:26]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>O1CCOCC1>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])[CH2:4][CH:3]1[C:18]1[N:22]2[C:23]3[CH:29]=[CH:28][N:27]([S:30]([C:33]4[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=4)(=[O:32])=[O:31])[C:24]=3[N:25]=[CH:26][C:21]2=[N:20][CH:19]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58010243HCID 58010243, compound

Product 1

HCID 58010113HCID 58010113, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of benzyl 4-methyl-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)piperidine-1-carboxylate (1.2 g, 2.2 mmol) in 1,4-dioxane (15 mL) was added Lawesson's reagent (0.44 g, 1.1 mmol) and the mixture was heated at about 60° C. for about 90 min. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography eluting with a gradient of 0-1.5% MeOH/DCM to yield benzyl 4-methyl-3-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)piperidine-1-carboxylate (0.93 g, 78%) as a yellow amorphous solid: LC/MS (Table 2, Method a) Rt=2.49 min; MS m/z: 544 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a gradient of 0-1.5% MeOH/DCM

Sources & evidence

ORD record
ord-0c3e6de7d1b7487284a6d136ceb09aae
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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