Methanol → HCID 10224798, compound

HRID 2185838Notes

Reaction equation

HRID 2185838 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]([C:28]#[N:29])[C:14](=[O:27])[NH:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].CO>CN(C=O)C>[O:27]=[C:14]1[C:13]([C:28]#[N:29])=[CH:12][C:11]([C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:10]=2)=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[NH:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6115AnilineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 15541009HCID 15541009, compound

Product 1

HCID 10224798HCID 10224798, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-(2-methylsulfonylpyrimidin-4-yl)-2-oxo-6-(3-trifluoromethylphenyl)-1,2-dihydropyridine-3-carbonitrile (160 mg, 0.35 mmol) in DMF, under argon, was added a prepared mixture of aniline (129 μL, 1.30 mmole) and potassium bis(trimethylsilyl)amide (0.5M in toluene) (2.6 mL, 1.30 mmole) under argon. The reaction was stirred for 15 minutes and then quenched into ethyl acetate and water. The pH was adjusted to 5.4 with aqueous potassium hydrogen sulfate solution and the ethyl acetate layer removed and concentrated to give a solid. Trituration of the solid from methanol (4 mL) gave 80 mg of a solid.

Workup

  1. customquenched into ethyl acetate and water
  2. customthe ethyl acetate layer removed
  3. concentrationconcentrated
  4. customto give a solid

Sources & evidence

ORD record
ord-642d5d438aaa4a5981e0a71a0dc43a3f
Source dataset
uspto-grants-2002_06
Patent number
US06403596B1

Reaction notes

Loading…