Lawesson's reagent → HCID 71731647, compound

HRID 1056145Notes

Reaction equation

HRID 1056145 reaction equation
[C:1]([NH:5][C:6]1[C:7]([CH3:26])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:24][C:23]3[CH2:22][CH2:21][NH:20][C:19](=O)[C:18]=3[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCOCC1>[C:1]([NH:5][C:6]1[C:7]([CH3:26])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:24][C:23]3[CH2:22][CH2:21][NH:20][C:19](=[S:36])[C:18]=3[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 71731146HCID 71731146, compound

Product 1

HCID 71731647HCID 71731647, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (193) (0.02 g, 0.057 mmol), Lawesson's reagent (Sigma-Aldrich) (0.028 g, 0.069 mmol), Dioxane (0.88 mL) was heated to 75° C. overnight. Reaction mixture was directly loaded onto prep-plate TLC. Purification (3% MeOH/DCM) provided 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridine-4(5H)-thione (292) (8 mg, 36% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.54-1.60 (m, 4H), 1.66 (s, 9H), 2.56 (s, 3H), 2.95-3.08 (m, 2H), 3.62-3.76 (m, 2H), 4.78-4.93 (m, 1H), 7.28-7.31 (m, 1H), 7.34-7.45 (m, 1H), 7.62-7.72 (m, 1H), 7.95-8.04 (m, 1H), 12.69-12.74 (m, 1H). m/z (ES, +ve) 366.3 (M+H)+.

Workup

  1. customReaction mixture
  2. customPurification (3% MeOH/DCM)

Sources & evidence

ORD record
ord-47d03a6edc2f403d88fab191f3f2ad02
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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