Lawesson's reagent → HCID 59619942, compound

HRID 445686Notes

Reaction equation

HRID 445686 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[C:19]3[C:18]4[CH:17]=[C:16]([C:20]5[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=5)[CH:15]=[CH:14][C:13]=4[N:12]=[CH:11][C:10]=3[N:9]([CH3:26])[C:8]2=O)[C:4]([CH3:28])=[N:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>O1CCOCC1>[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[C:19]3[C:18]4[CH:17]=[C:16]([C:20]5[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=5)[CH:15]=[CH:14][C:13]=4[N:12]=[CH:11][C:10]=3[N:9]([CH3:26])[C:8]2=[S:38])[C:4]([CH3:28])=[N:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 49835251HCID 49835251, compound

Product 1

HCID 59619942HCID 59619942, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of a new batch of 1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-8-pyridin-3-yl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Example 10.2, 8 mg, 0.219 mmol) and Lawesson's reagent (98 mg, 0.242 mmol) in dioxane (1 ml) was stirred in a seal vial for 28 h at 100° C. The reaction mixture was quenched with saturated aqueous NaHCO3 and extracted with DCM (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was taken in NMP and purified by Prep.HPLC (H2O (0.1% TFA)/CH3CN 95:5 to 65:35). The fractions containing products were collected together and basified with NaHCO3 (0.3 g), before being concentrated. The resulting suspension was filtered and the cake was washed with water, before being dried under high vacuum to give the title compound as a white solid. (HPLC: tR 2.32 min (Method A); M+H=387 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.21 (s, 1H), 8.72-8.68 (m, 1H), 8.62-8.58 (m, 1H), 8.23-8.16 (m, 2H), 8.08-8.04 (m, 1H), 7.93-7.88 (m, 1H), 7.56-7.48 (m, 2H), 3.97-3.93 (m, 6H), 1.92 (s, 3H))

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NaHCO3
  2. extractionextracted with DCM (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. custompurified by Prep.HPLC (H2O (0.1% TFA)/CH3CN 95:5 to 65:35)
  8. additionThe fractions containing products
  9. customwere collected together
  10. concentrationbefore being concentrated
  11. filtrationThe resulting suspension was filtered
  12. washthe cake was washed with water
  13. custombefore being dried under high vacuum

Sources & evidence

ORD record
ord-0f6d620ea4f64484a2e11b77c1074874
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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