Lawesson's reagent → HCID 11979153, compound

HRID 1971235Notes

Reaction equation

HRID 1971235 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:24]3[C:23]4[CH:22]=[C:21]([C:25]5[CH:26]=[N:27][C:28]6[C:33]([CH:34]=5)=[CH:32][CH:31]=[CH:30][CH:29]=6)[CH:20]=[CH:19][C:18]=4[N:17]=[CH:16][C:15]=3[N:14]([CH3:35])[C:13]2=O)=[CH:8][CH:7]=1)([CH3:5])[C:3]#[N:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1>O1CCOCC1>[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:24]3[C:23]4[CH:22]=[C:21]([C:25]5[CH:26]=[N:27][C:28]6[C:33]([CH:34]=5)=[CH:32][CH:31]=[CH:30][CH:29]=6)[CH:20]=[CH:19][C:18]=4[N:17]=[CH:16][C:15]=3[N:14]([CH3:35])[C:13]2=[S:46])=[CH:8][CH:7]=1)([CH3:5])[C:3]#[N:4]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 11977753Dactolisib

Product 1

HCID 11979153HCID 11979153, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

100 mg (0.213 mmol) of 2-methyl-2-[4-(3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-propionitrile (Example 7) and 95 mg (0.234 mmol) Lawesson reagent (Fluka, Buchs, Switzerland) in 1 ml of dioxane are heated at 100° C. for 96 h. The reaction mixture is quenched with sat. aqueous NaHCO3 and extracted with CH2Cl2 (2×). The organic layers are washed with sat. aqueous NaHCO3, dried over Na2SO4, filtered and evaporated. The residue is purified by preparative HPLC to provide the title compound as an off-white solid. ES-MS: 486 (M+H)+; analytical HPLC: tret=3.29 minutes (Grad 1).

Workup

  1. customThe reaction mixture is quenched with sat. aqueous NaHCO3
  2. extractionextracted with CH2Cl2 (2×)
  3. washThe organic layers are washed with sat. aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-dd685a63301b4d909a7af8a4120602ec
Source dataset
uspto-grants-2013_04
Patent number
US08431592B2

Reaction notes

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