Ethyl Acetate → HCID 86732402, compound

HRID 517277Notes

Reaction equation

HRID 517277 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].O=[C:8]1[NH:17][CH:16]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=2[S:26]([CH3:29])(=[O:28])=[O:27])[C:15]2[C:14](=[O:30])[CH2:13][CH2:12][CH2:11][C:10]=2[N:9]1[C:31]1[CH:36]=[CH:35][N:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:8][N:17]1[CH:16]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=2[S:26]([CH3:29])(=[O:27])=[O:28])[C:15]2[C:14](=[O:30])[CH2:13][CH2:12][CH2:11][C:10]=2[N:9]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([C:37]([F:40])([F:38])[F:39])[CH:32]=2)[C:1]1=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 86732403HCID 86732403, compound

Product 1

HCID 86732402HCID 86732402, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (265 mg, 0.82 mmol) and methyl idodide (51 μL, 0.82 mmol) are added to a solution of 4-(2,5-dioxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile (example 57, 200 mg, 0.41 mmol) in N,N-dimethylformamide (3 mL), and the mixture is stirred at room temperature for 2 h. Ethyl acetate is added, and the mixture is extracted three times with water. The organic phase is dried over Mg2SO4 and concentrated under reduced pressure. The residue is it) purified by flash chromatography on silica (gradient dichloromethane/methanol 99:1 to 97:3). Yield: 134 mg; ESI mass spectrum [M+H]+=505; Retention time HPLC: 0.60 min (X012_S02).

Workup

  1. extractionthe mixture is extracted three times with water
  2. dry with materialThe organic phase is dried over Mg2SO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash chromatography on silica (gradient dichloromethane/methanol 99:1 to 97:3)
  5. custom0.60 min (X012_S02)

Sources & evidence

ORD record
ord-de4f20aa68dc4412a4c44eed80f580e5
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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