HCID 117823951, compound → HCID 117824218, compound

HRID 59135Notes

Reaction equation

HRID 59135 reaction equation
[CH3:1][Mg]Br.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]2[N:24]=[C:23]([C:25](=[O:27])[CH3:26])[C:22]([CH3:28])=[C:21]([CH2:29][O:30][CH2:31][C:32]([F:35])([F:34])[F:33])[N:20]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1>C1COCC1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]2[N:24]=[C:23]([C:25]([OH:27])([CH3:1])[CH3:26])[C:22]([CH3:28])=[C:21]([CH2:29][O:30][CH2:31][C:32]([F:33])([F:34])[F:35])[N:20]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 117823951HCID 117823951, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 117824218HCID 117824218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (0.199 mL of 3M solution, 0.28 mmol) was added slowly to a solution of 1-(2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-5-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)ethanone (25 mg, 0.06 mmol) in THF (3 mL). The mixture was stirred at RT for 1 h. The mixture was quenched with saturated solution of ammonium chloride in water (1.5 mL) and diluted with brine (10 mL). The mixture was extracted with EtOAc (2×20 mL). The organic phase was dried over sodium sulfate and concentrated in vacuum. The residue was purified by preparative HPLC to give title compound as a dry film, 13 mg (45%).

Workup

  1. customThe mixture was quenched with saturated solution of ammonium chloride in water (1.5 mL)
  2. additiondiluted with brine (10 mL)
  3. extractionThe mixture was extracted with EtOAc (2×20 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6d3b126b228a46a0b086ab9d5f3bdfaa
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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