Water → HCID 178428419, compound

HRID 1484581Notes

Reaction equation

HRID 1484581 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:22]([F:25])([F:24])[F:23])=[C:5]([C:20]#[N:21])[CH:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[CH3:19])[C:7]=1[C:8]#[N:9].[C:26](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C=O)C.CO>[CH3:26][N:3]1[C:4]([C:22]([F:25])([F:23])[F:24])=[C:5]([C:20]#[N:21])[CH:6]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[CH3:19])[C:7]([C:8]#[N:9])=[C:2]1[CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 10796Cesium carbonate2×HCID 178428418rac-2-Methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile

Product 1

HCID 178428419HCID 178428419, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 375 mg (1.09 mmol) 2-methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile (Example 4) in DMF (11.5 ml) was cooled to 0° C. 534 mg (1.64 mmol) caesium carbonate were added at this temperature, and after 15 min 48 μl (0.77 mmol) methyl iodide were added dropwise at room temperature. After stirring overnight at rt, additional methyl iodide (20 μl) and a small amount of caesium carbonate were added, and the reaction mixture was stirred at rt for further 3 h before water and methanol were added. The resulting solution was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) to give 75 mg (19% of th.) of the racemic title compound.

Workup

  1. additionwere added
  2. customThe resulting solution was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-8ed8aaa222ae474ebf0fe0331fa0ee5e
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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