Water → HCID 90310897, compound

HRID 927243Notes

Reaction equation

HRID 927243 reaction equation
CI.[O:3]=[C:4]1[N:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[C:8]2[CH2:20][CH2:21][C:22](=[O:23])[C:7]=2[CH:6]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=2[S:32]([CH3:35])(=[O:34])=[O:33])[NH:5]1.[C:36](=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:36][N:5]1[CH:6]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=2[S:32]([CH3:35])(=[O:33])=[O:34])[C:7]2[C:22](=[O:23])[CH2:21][CH2:20][C:8]=2[N:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([F:17])([F:19])[F:18])[CH:11]=2)[C:4]1=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 90311070HCID 90311070, compound

Product 1

HCID 90310897HCID 90310897, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (2 M in tert-butyl methyl ether, 63 μL, 0.13 mmol) is added to a solution of 4-(2,5-dioxo-1-(2-(trifluoromethyl)pyridin-4-yl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)-3-(methylsulfonyl)benzonitrile (example 15.6, 50 mg, 0.11 mmol) and cesium carbonate (68 mg, 0.21 mmol) in N,N-dimethylformamide (2.0 mL), and the mixture is stirred at room temperature over night. Water is added and the mixture is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 39 mg; ESI mass spectrum [M+H]+=491; Retention time HPLC: 0.97 min (Z018_S04).

Workup

  1. customthe mixture is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  2. custom0.97 min (Z018_S04)

Sources & evidence

ORD record
ord-9a9a8c8ae2fa40378ba5c882f2346e36
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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