Lawesson's reagent → N,N-Dibenzyl-3-methyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclopentan-amine

HRID 1969586Notes

Reaction equation

HRID 1969586 reaction equation
[CH2:1]([N:8]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:9]1[CH2:13][CH:12]([C:14](=O)[CH2:15][NH:16][C:17]2[N:18]=[C:19]3[CH:25]=[CH:24][N:23]([S:26]([C:29]4[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=4)(=[O:28])=[O:27])[C:20]3=[N:21][CH:22]=2)[CH:11]([CH3:37])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>>[CH2:1]([N:8]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:9]1[CH2:13][CH:12]([C:14]2[N:18]3[C:19]4[CH:25]=[CH:24][N:23]([S:26]([C:29]5[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=5)(=[O:28])=[O:27])[C:20]=4[N:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH:11]([CH3:37])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 87949Lawesson's reagent2×HCID 585570961-(4-(dibenzylamino)-2-methylcyclopentyl)-2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)ethanone

Product 1

HCID 58557179N,N-Dibenzyl-3-methyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclopentan-amineYield 87%

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(4-(dibenzylamino)-2-methylcyclopentyl)-2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)ethanone (5.32 g, 8.75 mmol, Preparation #50) and Lawesson's reagent (1.88 g, 4.64 mmol) was heated at about 60° C. for about 2 h. Lawesson's reagent (1.88 g, 4.64 mmol) was added. The reaction mixture was stirred at about 60° C. for about 1 h. The solvent was removed under reduced pressure and the residue purified by silica gel flash chromatography eluting with a gradient of 0-8% MeOH in DCM to yield N,N-dibenzyl-3-methyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)cyclopentanamine (4.47 g, 87%) as a brown amorphous solid: LC/MS (Table 1, Method a) Rt=2.99 min; MS m/z 590 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by silica gel flash chromatography
  3. washeluting with a gradient of 0-8% MeOH in DCM

Sources & evidence

ORD record
ord-d3ace0d4133c46fca19bba6b8d5e42cd
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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