Lawesson's reagent → HCID 58382116, compound

HRID 1628012Notes

Reaction equation

HRID 1628012 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:24]=[C:23]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=4)[N:27]([CH3:36])[CH:26]=3)[N:22]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:19]2=[N:20][CH:21]=1)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:54])=CC=1>O1CCOCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12](=[S:54])[NH:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:24]=[C:23]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=4)[N:27]([CH3:36])[CH:26]=3)[N:22]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:19]2=[N:20][CH:21]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58382263HCID 58382263, compound

Product 1

HCID 58382116HCID 58382116, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A flask was charged with 4-(tert-butyldimethylsilyloxy)-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanamide (0.100 g, 0.157 mmol) and 1,4-dioxane (5 mL). Lawesson's Reagent (0.095 g, 0.235 mmol) was added and the mixture was stirred at about 85° C. for about 1 h. The mixture was cooled to rt, concentrated in vacuo and the residue was partitioned with EtOAc (10 mL) and saturated aqueous NaHCO3 (7 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 4-(tert-butyldimethylsilyloxy)-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanethioamide (0.103 g, 100%): LC/MS (Table 2, Method b) Rf=3.84 min; MS m/z 654 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated in vacuo
  3. customthe residue was partitioned with EtOAc (10 mL) and saturated aqueous NaHCO3 (7 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa153369d44645bf8197b8addb8f3287
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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