Cesium carbonate → HCID 86732404, compound

HRID 517278Notes

Reaction equation

HRID 517278 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][CH:19]=2)[C:15]2[C:14](=[O:26])[CH2:13][CH2:12][CH2:11][C:10]=2[N:9]1[C:27]1[CH:32]=[CH:31][N:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1>CN(C)C=O>[CH3:8][N:17]1[CH:16]([C:18]2[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=2)[C:15]2[C:14](=[O:26])[CH2:13][CH2:12][CH2:11][C:10]=2[N:9]([C:27]2[CH:32]=[CH:31][N:30]=[C:29]([C:33]([F:35])([F:34])[F:36])[CH:28]=2)[C:1]1=[O:4]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 86732405HCID 86732405, compound

Product 1

HCID 86732404HCID 86732404, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (39 mg, 0.12 mmol) and methyl idodide (6 μL, 0.10 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)benzonitrile (example 14, 25 mg, 61 μmol) in N,N-dimethylformamide (1 mL). The mixture is stirred at room temperature for 1 h, diluted with aceontrile and purified by preparative HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 13 mg; ESI mass spectrum [M+H]+=427; Retention time HPLC: 1.02 min (Z018_S04).

Workup

  1. additiondiluted with aceontrile and
  2. custompurified by preparative HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  3. custom1.02 min (Z018_S04)

Sources & evidence

ORD record
ord-8d1f784f21e24522b30696603cbc07b7
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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