Cesium carbonate → HCID 90310845, compound

HRID 927241Notes

Reaction equation

HRID 927241 reaction equation
[F:1][CH:2]([F:32])[C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[CH2:15][CH2:16][C:17](=[O:18])[C:13]=3[CH:12]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=3[S:27]([CH3:30])(=[O:29])=[O:28])[NH:11][C:10]2=[O:31])[CH:6]=[CH:7][CH:8]=1.[C:33](=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[F:32][CH:2]([F:1])[C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[CH2:15][CH2:16][C:17](=[O:18])[C:13]=3[CH:12]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=3[S:27]([CH3:30])(=[O:29])=[O:28])[N:11]([CH3:33])[C:10]2=[O:31])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 90310805HCID 90310805, compound

Product 1

HCID 90310845HCID 90310845, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl idodide (15 μL, 0.24 mmol) is added to a solution of 4-(1-(3-(difluoromethyl)-phenyl)-2,5-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)-3-(methyl-sulfonyl)benzonitrile (example 15.4, 69 mg, 0.15 mmol) and cesium carbonate (98 mg, 0.30 mmol) in N,N-dimethylformamide (1.0 mL). The mixture is stirred at room temperature for 1 h and purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 19 mg; ESI mass spectrum [M+H]+=472; Retention time HPLC: 0.97 min (Z018_S04).

Workup

  1. custompurified 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-a23f54b01ab84d0abdbfb9a84a0bac08
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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